Tamari Narindoshvili

University of Florida, Gainesville, FL, United States

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Publications (13)33.93 Total impact

  • Alan R. Katritzky, Geeta Meher, Tamari Narindoshvili
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    ABSTRACT: 5-(Substituted amino)-1,2,3,4-thiatriazoles 15a – 15i were conveniently synthesized in 73–97% yields in a one-pot procedure from bis(1 H -benzotriazol-1-yl)methanethione and amines.
    ChemInform 01/2010; 41(5).
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    Alan R Katritzky, Davit Jishkariani, Tamari Narindoshvili
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    ABSTRACT: DL-Ibuprofen and L-naproxen were coupled with amino acids and other bioactive compounds to provide ibuprofen and naproxen bioconjugates in 61-95% yield as prodrugs or potential drug candidates.
    Chemical Biology &amp Drug Design 07/2009; 73(6):618-26. · 2.47 Impact Factor
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    Alan Roy Katritzky, Tamari Narindoshvili
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    ABSTRACT: Fluorescent labeling is today of paramount importance to biological studies and numerous chemical dyes are used extensively to label biological specimens. This perspective highlights interesting aspects of fluorescent labeling by fluorescent peptides and small organic fluorophores that can be incorporated into proteins by genetic fusion to produce a fluorescent label. While many fluorescence applications rely on the use of intrinsic fluorophores, the development of new extrinsic fluorophores remains an essential element for the design of new fluorescent probes.
    Organic & Biomolecular Chemistry 03/2009; 7(4):627-34. · 3.57 Impact Factor
  • Alan Roy Katritzky, Tamari Narindoshvili
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    ABSTRACT: 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.
    ChemInform 01/2009; 40(21).
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    ABSTRACT: N(alpha)-Fmoc-N(epsilon)-[(7-methoxycoumarin-4-yl)acetyl]-L-lysine (N(alpha)-Fmoc-L-Lys(Mca)-OH) 3 is conveniently prepared by benzotriazole methodology (52% over two steps). N-Acylbenzotriazoles Mca-Bt 2, N(alpha)-Fmoc-L-Lys(Mca)-Bt 4, coumarin-3-ylcarbonyl (Cc)-Bt 5, N(alpha)-Fmoc-L-Lys(Cc)-Bt 7 and N(alpha)-(Cc)-L-Lys(Fmoc)-Bt 9 enable the efficient microwave enhanced solid-phase fluorescent labeling of peptides.
    Organic & Biomolecular Chemistry 01/2009; 6(24):4582-6. · 3.57 Impact Factor
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    Alan Roy Katritzky, Tamari Narindoshvili
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    ABSTRACT: Convenient high yielding syntheses of optically pure PNAMs comprising l- or d-serine, l-lysine and l-arginine units linked to thymine or Cbz-cytosine are described. Simple workup and inexpensive reagents are employed and free amino acids are used as coupling components.
    Organic & Biomolecular Chemistry 10/2008; 6(17):3171-6. · 3.57 Impact Factor
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    Alan R Katritzky, Geeta Meher, Tamari Narindoshvili
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    ABSTRACT: L-N(omega)-nitroarginine and L-arginine were coupled with N-(Cbz-alpha-aminoacyl)benzotriazoles and N-Cbz-dipeptidoylbenzotriazoles to provide arginine LL-dipeptides 9a-e, 11a-d; LLL-tripeptides 18a-c, 20; and diastereomeric mixtures (9b+9b'), (9c+9c'), (11b+11b') and (18c+18c') [compound numbers written within parentheses represent a diastereomeric mixture or racemate; compound numbers without parentheses represent an achiral compound or a single enantiomer] by extension at the N-terminus of arginine, in isolated yields of 66-95% with complete retention of chirality as evidenced by NMR and HPLC analysis. Arginine LL-dipeptides 15a-d were synthesized by extension at the C-terminus of arginine in isolated yield of 66-80%, using benzotriazole activated arginine L-(omega)NO2-Arg-Bt, 13. Our methodology has also been used to synthesize the protected RGD peptide (Cbz(alpha)-L-(omega)NO2-Arg-Gly-L-Asp-(OH)2) 21.
    The Journal of Organic Chemistry 09/2008; 73(18):7153-8. · 4.56 Impact Factor
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    ABSTRACT: N-Fmoc-protected(alpha-aminoacyl)benzotriazoles 1a-d readily afford chiral N-Fmoc-protected-alpha-dipeptides 2a-f (77-89%). Compounds 2a-f are further converted into N-Fmoc-protected(alpha-dipeptidoyl)benzotriazoles 3a-f (71% average yield). Under mild microwave irradiation, 3a-f are used in solid-phase peptide segment condensation syntheses to give tri-, tetra-, penta-, hexa-, and heptapeptides (20-68%).
    Chemical Biology &amp Drug Design 09/2008; 72(3):182-8. · 2.47 Impact Factor
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    Alan R Katritzky, Janet Cusido, Tamari Narindoshvili
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    ABSTRACT: Monosaccharides are fluorescently labeled under microwave irradiation by N-(coumarin-3-carbonyl)benzotriazole 4. 1,2:3,4-di- O-isopropylidene-alpha- d-galactopyranose 9 gives 12 (90%), 1,2:5,6-di- O-isopropylidene- d-glucose 10 gives 13 (89%), 2,3:5,6-di- O-isopropylidene-alpha- d-mannofuranose 11 gives 14 (65%) (all by O-acylation) and 2,3,4,5-tetra- O-pivaloyl-beta- d-galactopyranosylamine 15 gives 16 (60%) (by N-acylation). Similarly, the coumarin-containing activated lysine derivatives 7 and 8 afford the l-lysine-scaffold based coumarin labeled sugars 17, 18a, b, and 19 (67-85%) which, after removal of the diisopropylidene groups, provide water-soluble fluorescent derivatives.
    Bioconjugate Chemistry 08/2008; 19(7):1471-5. · 4.58 Impact Factor
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    ABSTRACT: Acylation of tetra-O-pivaloyl-beta-D-galactopyranosylamine 2 by readily available N- (Cbz or Fmoc-alpha-aminoacyl) benzotriazoles under microwave irradiation proceeded diastereoselectively to give beta-N-glycoaminoacids 3a-d, (3c+3c') (compound numbers written within brackets represent a racemate or a diastereomeric mixture; compound numbers without brackets represent a single enantiomer) (83-92%), and glycosylated asparagine building block 9 (65%). N-Cbz-Protected peptidoylbenzotriazoles 4a-c similarly afforded beta-N-glycodipeptides 5a-c (76-81%). Regiospecific beta-N-linkage formation was established by 1D and 2D NMR techniques for 3b.
    The Journal of Organic Chemistry 02/2008; 73(2):511-6. · 4.56 Impact Factor
  • Alan Katritzky, Tamari Narindoshvili, Parul Angrish
    Synthesis-stuttgart. 01/2008; 2008(13):2013-2022.
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    Alan R Katritzky, Parul Angrish, Tamari Narindoshvili
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    ABSTRACT: 1,2:3,4-Di-O-isopropylidene-alpha-D-galactopyranose (2), 1,2:5,6-di-O-isopropylidene-d-glucose (5), and 2,3:5,6-di-O-isopropylidene-alpha-D-mannofuranose (7) are efficiently O-acylated in 78-96% yields with readily available N-(Z-alpha-aminoacyl)benzotriazoles 1a-e, 1d+1d' under microwave irradiation to give chiral 3a-d, 4, 6a-d, 8a,b and diastereomeric mixtures (3d+3d'), (6a+6a'), and (6d+6d'). The original chirality was retained as evidenced by HPLC. The diisopropylidene protecting groups were removed from compounds 3a,d, 6d to give the free O-(Z-alpha-aminoacyl) sugars 9a,b, 10.
    Bioconjugate Chemistry 01/2007; 18(3):994-8. · 4.58 Impact Factor
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    Alan R Katritzky, Tamari Narindoshvili, Parul Angrish
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    ABSTRACT: N-(Coumarin-3-carbonyl)benzotriazole is coupled with free amino acids, N-terminal protected lysines, and dipeptides to afford fluorescent amino acids and dipeptides (yields 68-94%), with retention of original chirality. Coumarin-labeled lysines (19g, 21a,b, 22) are obtained by simple, two-step procedures. N -Coumarin-3-carbonyl-N -Cbz-L-lysine 21a is demonstrated to be an optically active fluorescence marker for labeling amino acids in solution phase syntheses. ε α Introduction The imaging of living cells is a big challenge in cell biology. Understanding the nature and dynamics of cel-lular events in living organisms is assisted by imaging cell components such as the nucleic acids, proteins and metabolites. Fluorescent markers are the visualization tools most commonly used, particularly fluorescent tag-ging with organic fluorophores 1 or green fluorescent protein (GFP). 2 Highly sensitive fluorescence derivatiza-tion techniques 3 are gaining an increasing share of the analytical world market, becoming competitive with, for example, radioimmunoassay. 4 Radioactive labeling of peptides usually involves the introduction of a radiolabeled amino acid as part of the natural structure of the peptide. In contrast, fluorescent tags are introduced as an additional moiety to the mole-cule, by a variety of strategies. 5-10 Derivatives of rhoda-mine, fluorescein, 11,12 and coumarin 13,14 are widely used as fluorescent markers for peptides and other bio-molecules. Xanthenes such as rhodamines, fluoresceins, and Alexa dyes are advantageously bright; however, drawbacks of existing derivatives in reporting protein conformational changes include (i) relatively long, flexi-ble linkers between the probe and protein, which ques-tions whether the probe motions faithfully mirror the motions of the residue to which it is attached; (ii) multi-ple charges and relatively large surface areas, which can perturb local structure or motion, and inhibit labeling at certain positions. 7, 13 Coumarins (benzopyranones), the largest class of laser dyes for the "blue-green" region 14-22 are highly sensitive. They have provided the most commercially acceptable categories of fluorescent derivatives with the advantages of an extended spectral range, high emission quantum yield, photostability, and good solubility in many sol-vents. The many bioanalytical applications of fluorescently labeled proteins include in vitro and vivo imaging, 6,23 high-throughput screening, 24 proteomics, 24-26 diagnos-tics, 9,27,28 single biomolecule spectroscopy, 26,29 HPLC control 30 and exploring protein conformations. 7 Probes for studying protein dynamics and electrostatics should be (i) sensitive to the state of hydrogen bonding in the solvent environment 31 and (ii) readily incorporated regiospecifically at the C or the N-terminus of a protein. The use of an amino acid as a fluorescent chromophore offers a good possibility to synthesize fluorescent pep-tides by solid-phase peptide synthesis (SPPS).