A general and expedient method based on a click reaction has been developed for the synthesis of novel glycolipids. The Cu(I) catalyzed [3+2] cycloaddition of several fully acetylated β- as well as α-d-glycopyranosyl azides, including the 1,6-diazide derived from d-glucose, with long chain alkyl propargyl ethers gave the respective 1,4-substituted 1,2,3-triazole derivatives in good yields. Treatment of fully acetylated N-(β-glycopyranosyl)azidoacetamides under similar conditions with alkyl propargyl ethers afforded the 1,2,3-triazolylacetamido derivatives in fairly good yields. Zemplen de-O-acetylation of all the fully acetylated derivatives furnished the free glycolipids in quantitative yields. © 2008 Elsevier Ltd. All rights reserved.

Katuri J V Paul

Duraikkannu Loganathan

1,2,3 TRIAZOLE DERIVATIVE

amide

Azide

cuprous ion

ETHER LIPID

glucose

glycolipid

GLYCOPYRANOSYL AZIDE

N (BETA GLYCOPYRANOSYL)AZIDOACETAMIDE

unclassified drug

ACETYLATION

article

catalysis

Cycloaddition

drug structure

lipogenesis

IIT Madras is a public technical and research university located in Chennai, Tamil Nadu. Founded in 1959, it is recognised as an Institute of National Importance.

IIT Madras has been ranked as the top engineering institute in India for four years in a row by the National Institutional Ranking Framework of the MHRD

It currently offers undergraduate, postgraduate and research degrees across 16 disciplines in Engineering, Sciences, Humanities and Management. About 596 faculty belonging to science and engineering departments and centres of the Institute are engaged in teaching, research and industrial consultancy.

IIT Madras

Tetrahedron Letters

A series of novel haloglycolipids were synthesized based on Cu(i) catalyzed Huisgen's [3 + 2] cycloaddition reaction of diversely functionalized azides and alkynes, using a mixture of N-bromosuccinimide and Cu(i) halide as the halogen source. Since halogen atoms, like bromine and iodine, with a very high scattering power facilitate the solving of crystal structures, the title haloglycolipids could prove to be invaluable in structure-based drug design involving membrane proteins as targets. This journal is © the Partner Organisations 2014.

Organic and Biomolecular Chemistry

Diversity oriented synthesis of novel haloglycolipids potentially useful for crystallization of integral membrane proteins

The torsion angle around the N-glycoprotein linkage region (GlcNAc-Asn) is an important factor for presenting sugar on the cell surface which is crucial for many biological processes. Earlier studies using model and analogs showed that this important torsion angle is greatly influenced by substitutions in the sugar part. In the present work, uronic acid alkanamides and triazole derivatives have been designed and synthesized as newer analogs of N-glycoprotein linkage region to understand the influence of the carboxylic group on linkage region torsion as well as on molecular packing. Crystal structure of N-(β-d-galacturonopyranosyl)acetamide is solved with the space group of P22121. Comparison of the torsion angle and molecular packing of this compound with N-(β-d-galactopyranosyl)acetamide showed that changing the C6-hydoxymethyl group to the carboxylic acid group has minimum influence on the N-glycosidic torsion angle, ΦN and significant influence on the molecular packing. © 2013 Elsevier Ltd. All rights reserved.

Carbohydrate Research

Synthesis of N-(β-d-glycuronopyranosyl)alkanamides and 1-(β-d-glycuronopyranosyl)-4-phenyl-[1,2,3]-triazoles as N-glycoprotein linkage region analogs: Examination of the effect of C5 substituent on the N-glycosidic torsion (ΦN) based on X-ray crystallography

A method for the chemoselective reduction of glycopyranosyl azides using SnCl4 and tin metal as the reducing agent followed by in situ chloroacetylation of the synthesized glycopyranosyl amine was developed. This reaction is applicable to diversely functionalized glycopyranosyl azides for the synthesis of glycopyranosyl chloroacetamides. © 2013 Elsevier Ltd. All rights reserved.

SnCl4/Sn catalyzed chemoselective reduction of glycopyranosyl azides for the synthesis of diversely functionalized glycopyranosyl chloroacetamides

N-(β-Glycopyranosyl)azidoacetamides, mimetics of the widely distributed GlcNAc-Asn linkage in glycoproteins, have been synthesized in good yields starting from β-glycopyranosylamines in four steps involving selective N-chloroacetylation, peracetylation catalyzed by Na β-zeolite, displacement of the Cl group by NaN3 in aqueous acetone, and Zemplen de-O-acetylation. Copyright © Taylor &amp; Francis, Inc.

Journal of Carbohydrate Chemistry

Synthesis of N-(β-Glycopyranosyl)azidoacetamides

Highly stereoselective synthesis of peracylated α-aldopyranosyl chlorides from aldopyranose peracetates and thionyl chloride catalyzed by BiCl3 generated in situ from the procatalyst BiOCl

Chemical Reviews

Bolaamphiphiles

Biochimica et Biophysica Acta (BBA) - Biomembranes

Stability and solubility of integral membrane proteins from photosynthetic bacteria solubilized in different detergents

Angewandte Chemie International Edition

A Stepwise Huisgen Cycloaddition Process: Copper(I)-Catalyzed Regioselective “Ligation” of Azides and Terminal Alkynes

Synthesis of novel glycolipids derived from glycopyranosyl azides and N-(β-glycopyranosyl)azidoacetamides

Journal	Tetrahedron Letters
ISSN	00404039
Open Access	No