Matthieu Sollogoub

• Prof, Dr
• Professor (Full) at Sorbonne University

NHC-capped cyclodextrin (ICyD) ligands, α-ICyD and β-ICyD derived from α- and β-cyclodextrin respectively give opposite regioselectivities in a copper-catalyzed hydroboration. The site-selectivity results from two different mechanisms: the conventional "parallel" one and a new "orthogonal" mechanism. The shape of the cavity was shown not only to in...

Access to Cn (n>4) symmetric cyclic concave molecules with a different function on each of their n subunits is an unmet challenge. The reason lies in the lack of a post-functionalization method whose site selectivity is sufficiently understood, predictable and modulable to access most functionalization patterns. Here we disclose a new site-directin...

Geschlossene Gesellschaft: Mit einem N-heterocyclischen Carben überdeckte Cyclodextrine (ICyDs) binden in ihrem Hohlraum Metallionen unter Beteiligung von X⋅⋅⋅π-Wechselwirkungen, was ein Verschließen des Hohlraums durch Ligandenaustausch ermöglicht (siehe Schema; Bn=Benzyl). Obwohl kein elektrischer Kontakt mit einer Elektrode besteht, behalten die...

Molecular mimicry is an essential part of the development of drugs and molecular probes. In the chemical glycobiology field, although many glycomimetics have been developed in the past years, it has been considered that many failures in their use are related to the lack of the anomeric effects in these analogues. Additionally, the origin of the ano...

The crystallization of a di-azido-α-cyclodextrin revealed a polymeric self-assembly involving a variety of azido-type interactions. The crystal arrangement relies on the cooperativity of a primary azido inclusion, a secondary azido–azido interaction involving an unprecedented distribution of canonical forms, and a tertiary azido–groove interaction....

The synthesis and evaluation of N‐heterocyclic carbene (NHC)‐capped cyclodextrins with various protecting groups were carried out. The corresponding gold complexes catalyze the stereoselective cycloisomerization of enynes. Permethylation of the cyclodextrin's hydroxyl groups improves yield and selectivity compared to its benzylated counterpart. Not...

The understanding of glycans, the third life chain, is widely desired. Naturally, the glycoconjugates are found in heterogeneous forms due to the enzyme competition in the same process. As a result, the synthesis of homogeneous glycans has become one of the trending research topics. In this review, orthogonal protection strategies were summarized t...

Herein, we describe the confinement of a N‐Heterocyclic Carbene (NHC) organocatalyst in the cavity of cyclodextrins (CDs). These confined organocatalysts allow the formylation of amines through CO2 hydrosilylation. The presence of the cavity of the CDs leads to substrate‐selectivity between amines in competition reactions. The use of the smallest α...

A functionnalized cyclodextrin can self-co-assemble with ds-DNA to form fibres of well-defined architecture. We have also determined the molecular structure of this abiotic assembly using cryo-EM and 3D image reconstruction.

Regioselective di‐functionalization of a cyclodextrin allows hydrophobic domains to be directed in a geometrically controlled manner. This controlled orientation ultimately gives access to an original hierarchical assembly in the solid state. This assembly spans over three levels of hierarchy which are governed by synergistic host‐guest inclusions,...

The Division de Chimie Organique (DCO) of the Société Chimique de France (SCF) and the European Journal of Organic Chemistry are coming together for the second consecutive year to celebrate the recipients of the 2021 DCO Awards. image

The development of organometallic catalysis has greatly expanded the synthetic chemist toolbox compared to only exploiting "classical" organic chemistry. Although more widely used in organic solvents, metal-based catalysts have also emerged as efficient tools for developing organic transformations in water, thus paving the way for further developme...

Cyclodextrin (β‐CD) and derivatives are approved therapeutics in >30 clinical settings. β‐CDs have also shown promise as therapeutics for treatment of some lysosomal storage disorders, such as Niemann‐Pick disease type C, and other disease states which involve metabolite accumulation in the lysosome. In these cases, β‐CD activity relies on transpor...

In the last few years, nanomaterials based on fullerene have begun to be considered promising tools in the development of efficient adjuvant/delivery systems for vaccination, thanks to their several advantages such as biocompatibility, size, and easy preparation and modification. In this work we reported the chemoenzymatic synthesis of natural poly...

Bis-azolium salts with one azolium capping a perbenzylated α-cyclodextrin have been designed to generate Janus-type bimetallic complexes with various combinations of copper, silver, gold or palladium salts. Encapsulation of one metal center inside the cavity allowed (trans)metalation and oxidation reactions to be controlled at selected positions. I...

In this chapter, metal complexes based on N -heterocyclic carbene (NHC)-capped cyclodextrins (CD) and their application for cavity-controlled catalysis are presented. In these complexes, the reactive metal center is encapsulated deep inside the CD cavity. First, the effect of NHC capping on the CD cavity shape and the positioning of the metal cente...

For the first time, the Division de Chimie Organique (DCO) of the Société Chimique de France (SCF) and the European Journal of Organic Chemistry join forces to celebrate the awardees of the Prix de la Division 2020. image

The encapsulation of guests in a confined space enables unusual conformations and reactivities. In particular, the compression of akyl chains has been obtained by self-assembled molecular capsules but such an effect has not been reported in solution for pseudorotaxane architectures. By exploiting the tendency of cyclodextrin (CD) to form head to he...

Encapsulation of a metal center inside the cavity of a cyclodextrin (CD) allows the control of the possible coordination modes for the metal depending on the nature and size of the cavity. We show here that the formation of encapsulated square planar AuIII and PdII complexes with CD‐N‐heterocyclic carbene (NHC) ligands, is only possible in the larg...

Mucopolysaccharidosis type IIIB is a devastating neurological disease caused by a lack of the lysosomal enzyme, α‐N‐acetylglucosaminidase (NAGLU), leading to a toxic accumulation of heparan sulfate. Herein we explored a pharmacological chaperone approach to enhance the residual activity of NAGLU in patient fibroblasts. Capitalizing on the three‐dim...

What happens when a C−H bond is forced to interact with unpaired pairs of electrons at a positively charged metal? Such interactions can be considered as “contra‐electrostatic” H‐bonds, which combine the familiar orbital interaction pattern characteristic for the covalent contribution to the conventional H‐bonding with an unusual contra‐electrostat...

Cyclodextrin poly‐functionalization has fueled progress in their use in multiple applications such as enzyme mimicry, but also in the polymer sciences, luminescence, as sensors or for biomedical applications. However, regioselective access to a given pattern of functions on β‐cyclodextrin is still very limited. We uncover a new orienting group, the...

Methods for regioselective access to a given pattern of functions on β-cyclodextrin remain limited. A thioacetate orienting group expands the toolbox available for cyclodextrin poly-hetero-functionalization using DIBAL-H promoted debenzylation. This method allowed the synthesis of a precisely hepta-hetero-functionalized β-cyclodextrin. A random hep...

Water‐soluble NHC‐capped permethylated cyclodextrins with encapsulated copper(I), silver(I), or gold(I) complexes were used as catalysts in neat water for hydration, lactonization, hydroarylation, and cycloisomerization reactions. The cavity of these ligands induced high regioselectivity in hydroarylations, and high enantioselectivities in gold‐cat...

A series of water‐soluble encapsulated copper(I), silver(I) or gold(I) complexes based on NHC‐capped permethylated cyclodextrins (ICyDMe) were developed and used as catalysts in pure water for hydration, lactonization, hydroarylation and cycloisomerization reactions. ICyDMe ligands gave cavity‐based high regioselectivity in hydroarylations, and hig...

Ganglioside GM3 has a strong impact on the occurrence and development of human cancer. GM3 is not only overexpressed in several types of cancer but also inhibits tumor cell growth through anti-angiogenesis or motility. In particular, the effect of GM3 on EGFR tyrosine kinase signaling is essential for cancer. GM3 analogs showed better tumor-suppres...

Glycosphingolipids (GSLs) are ubiquitous components on animal cell membranes, and exposed on the outer surface. Various studies have demonstrated that they play key roles in cells proliferation, adhesion, motility and differentiation. Usually, the specific types of GSLs are expressed more highly in tumors than in normal tissues, which are known as...

Mycobacteria infection resulting in tuberculosis (TB) is one of the top ten leading causes of death worldwide in 2018, and lipoarabinomannan (LAM) has been confirmed to be the most important antigenic oligosaccharide on the TB cell surface. In this study, a convenient synthetic method has been developed for synthesizing three branched oligosacchari...

Fluorinated carbohydrates have become indispensable in glycosciences. This contribution provides an overview of how fluorine introduction modifies physical and chemical properties of carbohydrates along with selected examples of its applications.

NHC-capped β-cyclodextrin (β-ICyD) was used as a ligand for gold-catalyzed alkoxycyclization reactions. The cavity was found to be responsible for a triple selectivity: (i) the asymmetric shape of the cavity of β-ICyD induced highly stereoselective cyclizations, (ii) the shape of the interior favored the formation of a six-membered ring in the abse...

Abstract: What happens when a C−H bond is forced to interact with unpaired pairs of electrons at a positively charged metal? Such interactions can be considered as “contra-electrostatic” H-bonds, which combine the familiar orbital interaction pattern characteristic for the covalent contribution to the conventional H-bonding with an unusual contra-e...

The Cover Feature shows kids (chemists) building blocks with monosaccharides “building blocks” through a convenient method. The key steps for stereoselective construction of glycosidic bonds by acceptors glycosylated with donors without neighboring participating group were achieved. After several steps and one step birch reaction, 5 oligosaccharide...

Retaining glycoside hydrolases cleave their substrates through stereochemical retention at the anomeric position. Typically, this involves two-step mechanisms using either an enzymatic nucleophile via a covalent glycosyl enzyme intermediate or neighboring-group participation by a substrate-borne 2-acetamido neighboring group via an oxazoline interm...

The encapsulation of copper inside a cyclodextrin capped with an N‐heterocyclic carbene (ICyD) allowed both to catch the elusive monomeric (L)CuH and a cavity‐controlled chemoselective copper‐catalyzed hydrosilylation of α,β‐unsaturated ketones. Remarkably, (α‐ICyD)CuCl promoted the 1,2‐addition exclusively, while (β‐ICyD)CuCl produced the fully re...

A new family of chiral C2 symmetric tetraazamacrocycles, coined ISAC for IminoSugar Aza-Crown, incorporating two iminosugars adopting a 4C1 conformation is disclosed. Multinuclear NMR experiments on the corresponding Cd2+ complex show that the ISAC is a strong chelator in water and its tetramine cavity adopts a conformation similar to that of the p...

Mycobacteria infection resulting in tuberculosis (TB) is one of the top ten leading causes of death over the world, and lipoarabinomannan (LAM) has been confirmed to play significant roles in this process. In this study, a convenient synthetic approach has been developed for the synthesis of oligosaccharides derived from LAM starting with commercia...

Hohl-in-One: Die Hohlraum-kontrollierte chemoselektive Kupfer-katalysierte 1,2- bzw. 1,4-Hydrosilylierung von α,β-ungesättigten Ketonen wurde in NHC-gedeckelten Cyclodextrinen (ICyDs) beobachtet. Im Hohlraum befindet sich eine seltene, intermediäre, monomere (L)CuH-Gruppe. Abstract The encapsulation of copper inside a cyclodextrin capped with an N...

Ganglioside GM3 is well known as a tumor-associated carbohydrate antigen on several types of tumors. Many studies have demonstrated that GM3 plays roles in cells proliferation, adhesion, motility and differentiation, which is involved in the process of cancer development. In the present study, we developed methods to synthesize GM3 analogues conven...

div>Retaining glycoside hydrolases cleave glycoconjugates into their component sugars through stereochemical retention at the anomeric position. Typically, this involves two-step mechanisms using either an enzymatic nucleophile via a covalent glycosyl enzyme intermediate, or neighboring group participation by a substrate-borne 2-acetamido neighbori...

Among the various types of chirality (central, axial, helical, planar…), that inherent to Möbius topology remains almost unex-plored, partly due to the difficulty to access Möbius compounds. Over the last decade, [28]hexaphyrins have revealed among the best candidates to build on Möbius aromaticity. Whereas their flexibility needs to be controlled...

Highly regioselective deprotection of a series of 2‐amino pyranose building blocks was achieved by enzymatic hydrolysis. These monodeprotected intermediates were successfully used in the synthesis of a variety of glycoconjugate derivatives with a core of glucosamine or galactosamine, including neo‐glycoproteins and glycosphingolipids. The hydrolysi...

The copper‐catalyzed carboboration of various alkynes was investigated with a modified N‐heterocyclic carbene‐capped α‐cyclodextrin copper(I) complex in which the reactive copper center is deeply encapsulated in the cyclodextrin (CD) cavity. The methylborylation of terminal alkynes was found to give linear (L) (E)‐vinyl boron isomers as the major i...

Ganglioside GM3, belonging to glycosphingolipid family, has been known as tumor-associated carbohydrate antigen on several types of tumor. Many studies have revealed that GM3 plays a role in cell proliferation, adhesion and differentiation, which is crucial in the process of cancer development. In the present study, we firstly synthesized novel man...

While an epoxide on a sugar-derived aziridine studying was opened, an unexpected formation of bicyclic compounds was observed. The structure of these bicycles depended on the nature of the protecting group on the nitrogen atom of the aziridine. These compounds appeared to be weak glycosidase inhibitors.

Ranking above AIDS, tuberculosis (TB) is the ninth leading cause of death affecting and killing many individuals every year. Drugs' efficacy is limited by serials of problems such as multi-drug resistance (MDR) and extensively-drug resistance (XDR). Meanwhile, the only licensed vaccine BCG (Bacillus Calmette-Guérin) existing for over 90 years is no...

Understanding the enzyme reaction mechanism can lead to the design of enzyme inhibitors. A Claisen rearrangement was used to allow conversion of an α-1,4-disaccharide into an α-1,3-linked glycosyl carbasugar to target the endo-α-mannosidase from the GH99 glycosidase family, which, unusually, is believed to act through a 1,2-anhydrosugar "epoxide" i...

Human African trypanosomiasis, or sleeping sickness, is a lethal disease caused by the protozoan parasite Trypanosoma brucei. However, although many efforts have been made to understand the biochemistry of this parasite, drug development has led to treatments that are of limited efficiency and of great toxicity. To develop new drugs, new targets mu...

Caging N‐heterocyclic carbene (NHC)–metal complexes in molecular or polymeric structures can confer them with interesting properties. In their Minireview on page 12464 ff., S. Roland, J. M. Suarez and M. Sollogoub discuss the benefits of caging for the selectivity of reactions catalyzed by such confined NHC–metal complexes. The confinement has been...

Confinement of a metal complex is a promising way to induce reactivity modulation and selectivity. Combining this principle with the properties of N-heterocyclic carbenes (NHC) used as ligands is therefore of great interest. NHCs metal complexes have been encapsulated in polymeric structures (metal-organic frameworks, metal organic polymers and por...

Targeting adaptive receptors for allosteric enzyme mimicry, sandwich hybrids composed of a hexaphyrin capped by two cyclodextrins have been synthesized. The hexaphyrin behaves as a dual-responsive device which couples the two cyclodextrins in a switchable manner through redox ([anti]aromaticity) and thermal (conformation) control. Conformational is...

The most common fullerene member C60 displays many biological applications, such as, anticancer, human immunodeficiency virus and hepatitis C virus inhibitors, O2 uptake inhibitor and vectors for drug and DNA. Nevertheless, the innate hydrophobicity of C60 constrains its further development. We introduced cyclodextrins to enhance the water-solubili...

To imitate Nature's ability to form cooperative self‐assemblies using entirely artificial molecular tools and to confer them with properties is still a true challenge. Here we show that cyclodextrins bridged with an ammonium linker which bears a hydrophobic substituent efficiently form supramolecular polymers at millimolar concentrations, avoiding...

To imitate Nature's ability to form cooperative self‐assemblies using entirely artificial molecular tools and to confer them with properties is still a true challenge. Here we show that cyclodextrins bridged with an ammonium linker which bears a hydrophobic substituent efficiently form supramolecular polymers at millimolar concentrations, avoiding...

Ganglioside GM3 is implicated in a variety of physiological and pathological processes. Due to GM3 exposes on the outer surface of cell membranes, it is strongly associated with cell adhesion, motility and differentiation. Neurite outgrowth is a key process in the development of functional neuronal circuits and regeneration of the nervous system af...

Ganglioside GM3 is strongly related with human tumors, such as lung, brain cancers and melanomas, and more and more evidences have revealed that GM3 possesses powerful effects on cancer development and progression. GM3 is over expressed on several types of cancers, and can be as a tumor-associated carbohydrate antigen, used for immunotherapy of can...

Access to allosteric enzyme mimics that ideally associate communicating compartments for catalysis and regulation is still challenging. Whereas a sandwich "cavity-catalyst-cavity" approach, developed mainly with cyclodextrins and porphyrins, appears promising, its counterpart with hexaphyrins featuring rich conformation, aromaticity and coordinatio...

NHC-capped cyclodextrin (ICyD) ligands, α-ICyD and β-ICyD derived from α- and β-cyclodextrin respectively give opposite regioselectivities in a copper-catalyzed hydroboration. The site-selectivity results from two different mechanisms: the conventional "parallel" one and a new "orthogonal" mechanism. The shape of the cavity was shown not only to in...

Sustainability in chemical processes is a primary challenge for which catalysis is an obvious answer. This requirement is also associated with selectivity in the catalyzed chemical transformations. Hence, inspired by nature, the use of metals associated with molecular cavities as catalysts appears opportune. Here, we show that the capping of cyclod...

A series of capped metallo-cyclodextrins were synthesized, affording a variety of artificial chiral metallo-pockets through modulation of the space around the metal. Carbene ligands were used as caps to place a silver, gold or copper center at a well-defined location inside the cyclodextrin cavity. Multiple weak interactions involving the d10 metal...

DIBAL-H-mediated demethylation provides a novel method to access secondary-rim functionalized γ-cyclodextrin. 2A,3B-Dihydroxyl-per-O-methylated-γ-cyclodextrin has been obtained, whose conjugation with C60 allows access to the most water-soluble C60 conjugate described so far. The water solubility of 0.12 m (550 mg mL−1) is 150 times higher than tha...

Based on classical drug design theory, a novel series of gentiopicroside derivatives was designed and synthesized. All synthesized compounds were then biologically evaluated for their inhibition of influenza virus and anti-HCV activity in vitro. Some of the gentiopicroside derivatives, such as 11a, 13d and 16 showed interesting anti-influenza virus...

We describe the potentiality of a new liposomal formulation enabling PET and MR imaging for cancer diagnosis. The bimodality is achieved by coupling a 68Ga-based radiotracer on the bilayer of ultra magnetic liposomes. In order to enhance the targeting properties obtained under a permanent magnetic field, a sugar moiety was added in the lipid formul...

Inhibitor design incorporating features of the reaction coordinate and transition-state structure has emerged as a powerful approach for the development of enzyme inhibitors. Such inhibitors find use as mechanistic probes, chemical biology tools and therapeutics. Endo-α-1,2-mannosidases and endo-α-1,2-mannanases, members of glycoside hydrolase fami...

Gentiopicroside is a secoiridoid compound isolated from Gentiana lutea which is called Qin Jiao in Chinese. It is one of the most common herbal medicines used in China. In this article, we review the pharmacological and biological activity (antiviral, anti-inflammatory, analgesia, antihepatotoxic and choleretic), as well as biotransformation of the...

Protonation study of [26/28]hexaphyrin-capped cyclodextrins revealed a temperature controlled conformational transition of the cap. The hexaphyrin undergoes a rectangular-Protonation study of [26/28]hexaphyrin-capped cyclodextrins revealed a temperature controlled conformational transition of the cap. The hexaphyrin undergoes a rectangular-to-trian...

The synthesis of new biobased polyamides from different β-cyclodextrin monomers and the (Z) octadec-9-enedioic acid is investigated. The aim of this study is to design different sensors, having different sensibilities and selectivities to a set of various volatile organic compounds (VOC) relevant in the early detection of lung cancer. The sensors a...

Reactive oxygen species (ROS) generation and radical scavenging are dual properties of hydrophilic C60 derivatives (hC60s). hC60s eliminate radicals in dark, while they produce reactive oxygen species (ROS) in the presence of irradiation and oxygen. Compared to the pristine C60 suspension, the aqueous solution of hC60s is easier to handle in vivo....

Conformational control over the highly flexible π-conjugated system of expanded porphyrins is a key step toward the fundamental understanding of aromaticity and for the development of molecular electronics. We have synthesized unprecedented hexaphyrin-cyclodextrin (HCD) capped hybrids in which the hexaphyrin part is constrained in a planar rectangu...

Sugar function, structure and dynamics are intricately correlated. Ring flexibility is intrinsically related to biological activity; actually plasticity in L-iduronic rings modulates their interactions with biological receptors. However, the access to the experimental values of the energy barriers and free-energy difference for conformer interconve...

A series of pentahydroxylated pyrrolidines, displaying five contiguous stereogenic centres and epimeric to α-glucosidase inhibitor homoDMDP, have been synthesized. The key step involves a γ-aminoalcohol rearrangement applied to polyhydroxylated azepanes. These five-membered iminosugars demonstrate micromolar inhibition of glycosidases.

Four novel 2-(trimethylsilyl)ethyl glycosides have been synthesized by a short and efficient route starting from d-glucose. Their structures were elucidated by applying high-resolution mass spectra, and one-dimensional and two-dimensional NMR techniques. These glycosides were prepared and used as intermediate building blocks in the scheme developed...

Cyclodextrins associated to metal centers or cyclodextrin–metal hybrids have been developed for a very long time mainly because this association was seen as potentially mimicking metallo-enzymes. To generate such mimics it is necessary to functionalize cyclodextrins with multiple functions; this chapter presents the most frequently used and recent...

The synthesis of 1,2-cis-homoiminosugars bearing an NHAc group at the C-2 position is described. The key step to prepare these a-d-GlcNAc and a-d-GalNAc mimics utilizes a beta-amino alcohol skeletal rearrangement applied to an azepane precursor. This strategy also allows access to naturally occurring a-HGJ and a-HNJ. The a-d-GlcNAc-configured imino...

The synthesis of 1,2-cis-homoiminosugars bearing an NHAc group at the C-2 position is described. The key step to prepare these α-d-GlcNAc and α-d-GalNAc mimics utilizes a β-amino alcohol skeletal rearrangement applied to an azepane precursor. This strategy also allows access to naturally occurring α-HGJ and α-HNJ. The α-d-GlcNAc-configured iminosug...

The first synthesis of 1,2-trans-homoiminosugars devised as mimics of β-d-GlcNAc and α-d-ManNAc is described. Key steps include a regioselective azidolysis of a cyclic sulfite and a β-amino alcohol skeletal rearrangement applied to a polyhydroxylated azepane. The β-d-GlcNAc derivative has been coupled to serine to deliver an iminosugar C-amino acid...

Selectively functionalized cyclodextrins with a bodipy fluorescent tag or Gd3+ complex were synthetized and threaded onto a polyammonium chain to form polyrotaxanes. This modular supramolecular assembly makes an ideal platform for bimodal (fluorescent and MRI) imaging applications.

Molecular mimicry is an essential part of the development of drugs and molecular probes. In the chemical glycobiology field, although many glycomimetics have been developed in the past years, it has been considered that many failures in their use are related to the lack of the anomeric effects in these analogues. Additionally, the origin of the ano...

Cyclodextrin-adamantane conjugates have been prepared and their ability to form supramolecular polymers was tested. It appears that they are either insoluble when the link is too rigid or they form self-included derivatives inhibiting the formation of the polymer.

The crystallization of a di-azido-α-cyclodextrin revealed a polymeric self-assembly involving a variety of azido-type interactions. The crystal arrangement relies on the cooperativity of a primary azido inclusion, a secondary azido–azido interaction involving an unprecedented distribution of canonical forms, and a tertiary azido–groove interaction....

Glycosphingolipids are components of essentially all mammalian cell membranes and are involved in a variety of significant cellular functions, including proliferation, adhesion, motility and differentiation. Sialosyllactosylceramide (GM3) is known to inhibit the activation of epidermal growth factor receptor (EGFR). In the present study, an efficie...

Significance Lipofuscin accumulation in the retinal pigment epithelium (RPE) is a hallmark of aging. High lipofuscin levels in the RPE have been associated with retinal degeneration and blindness in Stargardt disease patients and animal models. Currently, there is no treatment to prevent and/or revert lipofuscin-driven retinal degenerative changes....

A concise and efficient synthetic route for preparation of four ganglioside GM3 analogues was described. The key step is a highly regioselective and stereoselective α-sialylation from a suitably protected glycoside acceptor with a sialyl xanthate to provide the sialo-oligosaccharide in good yield. The cytotoxic properties of the synthetic gangliosi...

To fulfill the promise offered by concave molecules such as cyclodextrins, there is a desperate need for efficient methods for multiple heterofunctionalization. We have developed several strategies for preparing heterofunctionalized cyclodextrins based on a newly discovered regioselective debenzylation reaction of sugars and an understanding of its...