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Vasanthakumar Ganga Ramu

Vasanthakumar Ganga Ramu
Aurobindo Pharma Limited

PhD

About

48
Publications
10,254
Reads
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627
Citations
Introduction
Highly motivated leader with vast experience in chemical and enzyme assisted organic synthesis. Over a period of time, I developed range of molecules for neurodegeneration, oncology, diabetes and other medical issues. To mention, the molecules which I worked on are Carfilzomib, Sincalide, GLP-1/2 analogs, Leuprolide, Lanreotide, Glucagon, Linaclotide, Romidepsin, etc. I believe in manufacturing quality API's and biopharmaceuticals, for various health issues which mankind are facing.
Additional affiliations
February 2015 - present
Biocon
Position
  • Principal Investigator
November 2005 - March 2007
Indian Institute of Science Bangalore
Position
  • Research Associate
August 2012 - January 2015
Omgene Lifesciences Pvt Ltd.,
Position
  • DGM API (R&D)
Description
  • Design, synthesis, and development of non-infringing routes for peptide based API’s
Education
August 2001 - September 2004
Bangalore University
Field of study

Publications

Publications (48)
Article
Kyotorphin (KTP, l-tyrosyl-l-arginine) is an endogenous analgesic neuropeptide first isolated from bovine brain in 1979. Previous studies have shown that kyotorphins possess anti-inflammatory and antimicrobial activity. Six kyotorphins—KTP-NH2, KTP–NH2–DL, ibuprofen-conjugated KTP (IbKTP), IbKTP-NH2, N-methyl-D-Tyr-L-Arg, and N-methyl-L-Tyr-D-Arg—w...
Patent
Racemization-free methods are disclosed for the synthesis of carfilzomib. Novel intermediates and methods of making carfilzomib employing fragment condensation using the novel intermediates are disclosed. Amorphous carrfilzomib and methods of making same are disclosed
Article
Full-text available
Chronic brain ischemia is a prominent risk factor for neurological dysfunction and progression for dementias, including Alzheimer’s disease (AD). In rats, permanent bilateral common carotid artery occlusion (2VO) causes a progressive neurodegeneration in the hippocampus, learning deficits and memory loss as it occurs in AD. Kyotorphin (KTP) is an e...
Article
Recently, a designed class of efficient analgesic drugs derived from an endogenous neuropeptide, kyotorphin (KTP, Tyr-Arg) combining C-terminal amidation (KTP-NH2) and N-terminal conjugation to ibuprofen (Ib), IbKTP-NH2, was developed. The Ib moiety is an enhancer of KTP-NH2 analgesic action. In the present study, we have tested the hypothesis that...
Article
Amidated kyotorphin (L-Tyr-L-Arg-NH2; KTP-NH2) causes analgesia when systemically administered. The lipophilic ibuprofen-conjugated derivative of KTP-NH2 has improved analgesic efficacy. However, fast degradation by peptidases impacts negatively in the pharmacodynamics of these drugs. In this work, selected derivatives of KTP and KTP-NH2 were synth...
Article
Full-text available
The synthesis of IbKTP-NH2 with reduction of racemization up to no detectable level has been achieved using 3-(diethoxyphosphoryloxy)-1,2,3-benzotriazin-4(3H)-one (DEPBT). Among all coupling systems tested, only DEPBT-mediated amide bond formation between N-alpha-acylated tyrosine and arginine without loss of optical purity.
Article
The polymer electrolyte membrane fuel cell (PEMFC) is one of today's most promising clean energy technologies in the search to overcome both the energy reserve crisis and environmental pollution and is now on the verge of commercialization. In PEMFCs, the oxygen reduction reaction (ORR) at the cathode is the kinetically slow process dominating the...
Article
Metallic copper nanoparticles have been efficiently dispersed and stabilized on nitrogen-doped carbon nanotubes. They are about 8-10 nm in diameter and highly resistant against bulk oxidation. Their catalytic activity and recyclability have been investigated in A(3)-type coupling reactions for the synthesis of propargylamines. It was easily possibl...
Article
Antimicrobial peptides (AMPs) are promising candidates as alternatives to conventional antibiotics for the treatment of resistant pathogens. In the last decades, new AMPs have been found from the cleavage of intact proteins with no antibacterial activity themselves. Bovine hemoglobin hydrolysis, for instance, results in AMPs and the minimal antimic...
Article
ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
Article
The interaction of papain with peptide immobilized on the Au surface altered the interfacial electron transfer resistant, charge transfer resistance (RCT), by preventing the redox species approaching the electrode was characterized by electrochemical impedance spectroscopy (EIS), AC voltammetry, cyclic voltammetry and surface plasmon resonance tech...
Data
Structures of biotin, bio-5′AMP and desthiobiotin. The ligand atoms are numbered as per the LPC/CSU software. (0.05 MB DOC)
Article
ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
Article
Full-text available
Fatty acids are indispensable constituents of mycolic acids that impart toughness & permeability barrier to the cell envelope of M. tuberculosis. Biotin is an essential co-factor for acetyl-CoA carboxylase (ACC) the enzyme involved in the synthesis of malonyl-CoA, a committed precursor, needed for fatty acid synthesis. Biotin carboxyl carrier prote...
Article
A simple and efficient method for the synthesis of 7,8‐diaminopelargonic acid, a key intermediate in the biotin biosynthesis pathway, is reported. The d‐desthiobiotin powder was dissolved in concentrated hydrochloric acid, and the solution was exposed to microwave radiation of 2.45 GHz for varying lengths of time ranging from 60 s to 2 min. The pro...
Article
Full-text available
Biotin is an essential enzyme cofactor required for carboxylation and transcarboxylation reactions. The absence of the biotin biosynthesis pathway in humans suggests that it can be an attractive target for the development of novel drugs against a number of pathogens. 7-Keto-8-aminopelargonic acid (KAPA) synthase (EC 2.3.1.47), the enzyme catalyzing...
Article
The indispensability of biotin for crucial processes like lipid biosynthesis coupled to the absence of the biotin biosynthesis pathway in humans make the enzymes of this pathway, attractive targets for development of novel drugs against numerous pathogens including M. tuberculosis. We report the spectral and kinetic characterization of the Mycobact...
Article
Syntheses of Nα-Fmoc-peptide azides employing acid chloride as well as mixed anhydride methods have been carried out. The resulting Fmoc-peptide azides prepared have been isolated as solids in good yield (75-92 %) and are found to be analytically pure. Further, long shelf life of N α-Fmoc-peptide azides makes them useful in the extension of peptide...
Article
An expedient synthetic approach to N-silylamines has been developed. The protocol, using TMS-Cl/zinc dust instead of BSA, is useful for the conversion of amines or amino acid esters to the corresponding silyl derivatives, followed by acylation with an acyl chloride or Fmoc-amino acid chloride to give the corresponding amide or peptide. This procedu...
Article
An efficient synthesis of p‐nitrophenyl‐(9‐fluorenylmethoxy carbonylamino) methyl carbamates using isocyanates derived from Fmoc‐amino acid azides and p‐nitrophenol in presence of an equimolar quantity of N‐ethyldiisopropyl amine is described. All the carbamates have been isolated as crystalline solids and are fully characterized. Further, their ut...
Article
Full-text available
An efficient synthesis of p-nitrophenyl-(9-fluorenylmethoxy, carbonylamino) methyl carbamates using isocyanates derived from Fmoc-amino acid azides and p-nitrophenol in presence of an equimolar quantity of N-ethyldiisopropyl amine is described. All the carbamates have been isolated as crystalline solids and are fully characterized. Further, their u...
Article
A new and efficient method for the homologation of urethane protected α-amino acids to its β-homomers by the Arndt-Eistert method using TBTU as a coupling agent is described. Several Fmoc-/Boc-/Z-protected α-amino diazoketone derivatives have been obtained as crystalline solids in good yield. The method is found to be rapid and stereospecific.
Article
The Curtius rearrangement of Fmoc-amino acid azides 1 was carried out in toluene by refluxing the solution for 30 min. The resulting isocyanates 2 have been isolated as crystalline solids and are fully characterized by IR, (1)H NMR, (13)C NMR, and mass spectra. They are found to be stable for several months when stored at 4 degrees C. The acyl azid...
Article
The synthesis of Fmoc protected amino acid hydroxamates using Fmoc-amino acid chlorides and magnesium oxide is described. The method is simple and efficient, results in complete conversion, and gives good yields and satisfactory purity.
Article
A simple and efficient protocol for Arndt-Eistert chain homologation of Fmoc-/Boc-/Z-alpha-amino acids using BOP or PyBOP as a coupling agent to the corresponding beta-amino acids, synthesizing the key intermediate alpha-diazoketones as crystalline solids in good yield is described.
Article
A simple, efficient and stereospecific approach for the homologation of urethane-protected alpha-amino acids to beta-amino acids by the Arndt-Eistert method employing Fmoc-/Boc-alpha-amino acid and 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyl-uronium hexafluorophosphate mixture for the acylation of diazomethane synthesizing the key intermediates F...
Article
Full-text available
A simple and concomitant esterification method for the synthesis of methyl, ethyl, t-butyl, benzyl, and 9-fluorenylmethyl esters of Fmoc-/Boc-/Z-beta-homoamino acids employing Fmoc-/Boc-/Z-alpha-aminodiazoketones by Wolff rearrangement is described. The method offers good yield with purity.
Article
Full-text available
The synthesis of peptides employing 9-fluorenylmethyl chloroformate (Fmoc-Cl) as a coupling agent has been described. The method is simple, efficient and rapid. All the peptides have been obtained in good yield (70–95%). Furthermore, both the1H NMR and the HPLC studies on Fmoc-Phg-Phe-OMe and Fmoc-D-Phg-Phe-OMe revealed that the coupling is free fr...
Article
A simple and concomitant esterification method for the synthesis of methyl, ethyl, t-butyl, benzyl, and 9-fluorenylmethyl esters of Fmoc-/Boc-/Z-beta-homoamino acids employing Fmoc-/Boc-/Z-alpha-aminodiazoketones by Wolff rearrangement is described. The method offers good yield with purity.
Article
Full-text available
The use of Boc2O as a coupling agent in the homologation of N-urethane protected-α-amino acid to its β-homomers by the Arndt–Eistert method is described. The homologation gives good yields without racemization. The use of Boc2O as a coupling agent not only allows the easy scale up of the process but also it is cost effective.
Article
Full-text available
The synthesis of C-protected esters of Boc-/Z-alpha,alpha-dialkylamino acids is accomplished by using alkyl/aryl chloroformate in presence of DMAP as a catalyst. The reaction proceeds through mixed carboxylic carbonic anhydride, which was monitored by IR. The reaction was clean and complete in about 2 hr. All the esters prepared have been obtained...
Article
The synthesis of C-protected esters of Boc- / Z-,-dialkylamino acids is accomplished by using alkyl / aryl chloroformate in presence of DMAP as a catalyst. The reaction proceeds through mixed carboxylic-carbonic anhydride, which was monitored by IR. The reaction was clean and complete in about 2 hr. All the esters prepared have been obtained in goo...
Article
Full-text available
A simple method for the synthesis of several amino acidbenzyl ester p-toluenesulfonate salts from thecorresponding amino acid and benzyl alcohol in presence of p-toluenesulfonic acid accelerated with microwave irradiation isdescribed. Under similar condition, the amino acid benzyl esterhydrochloride salts have also been obtained by using thionylchl...
Article
Full-text available
The Wolff rearrangement of α-diazoketones, derived from Fmoc-α-amino acids, under no base conditions on exposure to microwave irradiation for 40 to 60 sec to Fmoc-β-amino acids with retention of configuration in good yield (91–95%) is described.
Article
A simple method for the synthesis of Z-/Boc-/Fmoc-protected β-amino acids by the Arndt-Eistert approach employing p-toluenesulphonyl chloride for the activation of the carboxyl group of N -protected amino acid is described. The method is rapid and gave good yields with opitical purity.
Article
ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
Article
Full-text available
Amides of Z- and Boc protected amino acids have been prepared by using p-toluenesulphonyl chloride (TsCl) for the activation of carboxyl group. The resulting mixed carboxylic-sulphonic anhydride intermediate was treated in situ with an excess of 25% ammonia solution. All the amino acid amides prepared were obtained as crystalline solids in good yie...
Article
The synthesis of Fmoc amino acid azides starting from the corresponding protected amino acid and sodium azide (NaN3) by the mixed anhydride method using isobutoxycarbonyl chloride (IBC-C1) or by the acid chloride method is described. Isolated as crystalline solids, they are stable at room temperature, with a long shelf-life, as well as in aqueous w...

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