Synthesis of new ribosylated Asn building blocks as useful tools for glycopeptide and glycoprotein synthesis

被引：14

作者：

Bonache, M. Angeles ^{[1
,2
,3
]}

Nuti, Francesca ^{[1
,2
,3
]}

Isaad, Alexandra Le Chevalier ^{[1
,2
,3
]}

Real-Fernandez, Feliciana ^{[1
,2
,3
]}

Chelli, Mario ^{[1
,2
,3
]}

Rovero, Paolo ^{[1
,4
]}

Papini, Anna M. ^{[1
,2
,3
]}

机构：

[1] Univ Florence, Lab Peptide & Prot Chem & Biol PeptLab, I-50019 Sesto Fiorentino, FI, Italy

[2] Univ Florence, Dipartimento Chim Organ Ugo Schiff, I-50019 Sesto Fiorentino, FI, Italy

[3] Univ Florence, CNR, ICCOM, I-50019 Sesto Fiorentino, FI, Italy

[4] Univ Florence, Dipartimento Sci Farmaceut, I-50019 Sesto Fiorentino, FI, Italy

来源：

TETRAHEDRON LETTERS | 2009年 / 50卷 / 28期

关键词：

N-Glycosylated Asn for SPGPS; alpha- and beta-ribofuranose Asn; Triazine-based coupling reagent; NEPHRITOGENIC GLYCOPEPTIDE; LINKAGE; DERIVATIVES;

D O I：

10.1016/j.tetlet.2009.04.124

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We performed the first synthesis of new Asn derivatives bearing alpha- or beta-ribose as pure anomers, linked by an N-glycosidic bond, on the side chain of the Asn residue orthogonally protected for Fmoc/Bu-t SPPS, by an efficient five-step strategy with a global yield of 73% starting from D-ribose. These building blocks are obtained in a large scale and can be useful tools for glycopeptide and glycoproteins synthesis. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：4151 / 4153

页数：3

共 28 条

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