Approaches to Pyranuronic -Sugar Amino Acid Building Blocks of Peptidosaccharide Foldamers

被引：7

作者：

Goz, Viktoria Goldschmidt ^{[1
]}

Pinter, Istvan ^{[2
]}

Harmat, Veronika ^{[1
]}

Perczel, Andras ^{[1
,2
]}

机构：

[1] MTA ELTE Prot Modeling Res Grp, Pazmany Peter Setany 1-A, H-1117 Budapest, Hungary

[2] Eotvos Lorand Univ, Lab Struct Chem & Biol, Inst Chem, Pazmany Peter Setany 1-A, H-1117 Budapest, Hungary

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 2018卷 / 03期

关键词：

Sugar amino acids; Oximes; Peptidomimetics; Amino acids; Carbohydrates; Foldamers; OLIGOMERS; DERIVATIVES; REDUCTION; COMPENDIUM; SCAFFOLDS; CLEAVAGE; ACETAL;

D O I：

10.1002/ejoc.201701612

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Pyranuronic -sugar amino acids (-SAAs) are biocompatible and tuneable building blocks of foldamers and chimera-peptides. The scalable and economical total synthesis of two building blocks is described here. These C-4 epimers, Fmoc-GlcAPU(Me)-OH (7) and Fmoc-GalAPU(Me)-OH (8), which are suitable for solid phase peptide synthesis, were prepared via a common oxime intermediate 16. The new synthesis uses nine consecutive steps, starting from methyl -d-glucopyranoside (6). The synthesis is fine-tuned, optimized, and ready for large-scale and cost-efficient production.

引用

页码：355 / 361

页数：7

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