Synthesis of N-(fluoren-9-ylmethoxycarbonyl)glycopyranosylamine uronic acids

Laiqiang Ying, Jacquelyn Gervay-Hague

Research output: Contribution to journalArticle

20 Citations (Scopus)

Abstract

The synthesis of 10 N-(fluoren-9-ylmethoxycarbonyl)glycopyranosylamine uronic acids that are amenable to solid-phase synthesis is described. The general synthetic strategy involves initial incorporation of the protected amine, followed by selective TEMPO oxidation of C-6 hydroxyl groups to give the corresponding Fmoc-protected sugar amino acids. Amine incorporation may be accomplished from aminolysis of the free sugar or from glycosyl azide reduction. The reactions can be carried out on multigram scale, providing access to unique monomer units for future incorporation into combinatorial library syntheses.

Original languageEnglish (US)
Pages (from-to)367-375
Number of pages9
JournalCarbohydrate Research
Volume339
Issue number2
DOIs
StatePublished - Jan 22 2004

Fingerprint

Uronic Acids
Amines
Sugar Acids
Sugars
Solid-Phase Synthesis Techniques
Azides
Hydroxyl Radical
Amino Acids
Monomers
Oxidation
TEMPO

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry

Cite this

Synthesis of N-(fluoren-9-ylmethoxycarbonyl)glycopyranosylamine uronic acids. / Ying, Laiqiang; Gervay-Hague, Jacquelyn.

In: Carbohydrate Research, Vol. 339, No. 2, 22.01.2004, p. 367-375.

Research output: Contribution to journalArticle

@article{d6e9ca7fbfa24e02b9a1c28883719e1c,
title = "Synthesis of N-(fluoren-9-ylmethoxycarbonyl)glycopyranosylamine uronic acids",
abstract = "The synthesis of 10 N-(fluoren-9-ylmethoxycarbonyl)glycopyranosylamine uronic acids that are amenable to solid-phase synthesis is described. The general synthetic strategy involves initial incorporation of the protected amine, followed by selective TEMPO oxidation of C-6 hydroxyl groups to give the corresponding Fmoc-protected sugar amino acids. Amine incorporation may be accomplished from aminolysis of the free sugar or from glycosyl azide reduction. The reactions can be carried out on multigram scale, providing access to unique monomer units for future incorporation into combinatorial library syntheses.",
author = "Laiqiang Ying and Jacquelyn Gervay-Hague",
year = "2004",
month = "1",
day = "22",
doi = "10.1016/j.carres.2003.10.018",
language = "English (US)",
volume = "339",
pages = "367--375",
journal = "Carbohydrate Research",
issn = "0008-6215",
publisher = "Elsevier BV",
number = "2",

}

TY - JOUR

T1 - Synthesis of N-(fluoren-9-ylmethoxycarbonyl)glycopyranosylamine uronic acids

AU - Ying, Laiqiang

AU - Gervay-Hague, Jacquelyn

PY - 2004/1/22

Y1 - 2004/1/22

N2 - The synthesis of 10 N-(fluoren-9-ylmethoxycarbonyl)glycopyranosylamine uronic acids that are amenable to solid-phase synthesis is described. The general synthetic strategy involves initial incorporation of the protected amine, followed by selective TEMPO oxidation of C-6 hydroxyl groups to give the corresponding Fmoc-protected sugar amino acids. Amine incorporation may be accomplished from aminolysis of the free sugar or from glycosyl azide reduction. The reactions can be carried out on multigram scale, providing access to unique monomer units for future incorporation into combinatorial library syntheses.

AB - The synthesis of 10 N-(fluoren-9-ylmethoxycarbonyl)glycopyranosylamine uronic acids that are amenable to solid-phase synthesis is described. The general synthetic strategy involves initial incorporation of the protected amine, followed by selective TEMPO oxidation of C-6 hydroxyl groups to give the corresponding Fmoc-protected sugar amino acids. Amine incorporation may be accomplished from aminolysis of the free sugar or from glycosyl azide reduction. The reactions can be carried out on multigram scale, providing access to unique monomer units for future incorporation into combinatorial library syntheses.

UR - http://www.scopus.com/inward/record.url?scp=0346154803&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0346154803&partnerID=8YFLogxK

U2 - 10.1016/j.carres.2003.10.018

DO - 10.1016/j.carres.2003.10.018

M3 - Article

C2 - 14698895

AN - SCOPUS:0346154803

VL - 339

SP - 367

EP - 375

JO - Carbohydrate Research

JF - Carbohydrate Research

SN - 0008-6215

IS - 2

ER -