Solid phase synthesis of vancomycin mimics

Christopher J. Arnusch; Roland J. Pieters

doi:10.1002/ejoc.200300044

Solid phase synthesis of vancomycin mimics

Christopher J. Arnusch
, Roland J. Pieters

Research output: Contribution to journal › Article › peer-review

24 Scopus citations

Abstract

A solid phase synthesis of a model system of the DE ring system of vancomycin is described. The synthesis involved biocatalytic resolutions of unnatural amino acids, is compatible with conventional solid phase peptide synthesis and contains as the key step: an on-be.ad S_NAr cyclization. Binding of a cyclic peptide to the carboxylate of N-Ac-D-Ala was demonstrated.

Original language	English
Pages (from-to)	3131-3138
Number of pages	8
Journal	European Journal of Organic Chemistry
Issue number	16
DOIs	https://doi.org/10.1002/ejoc.200300044
State	Published - 11 Aug 2003
Externally published	Yes

Keywords

Antibiotics
Bioorganic chemistry
Cyclization
Peptides
Receptors

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry

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10.1002/ejoc.200300044

Cite this

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title = "Solid phase synthesis of vancomycin mimics",

abstract = "A solid phase synthesis of a model system of the DE ring system of vancomycin is described. The synthesis involved biocatalytic resolutions of unnatural amino acids, is compatible with conventional solid phase peptide synthesis and contains as the key step: an on-be.ad SNAr cyclization. Binding of a cyclic peptide to the carboxylate of N-Ac-D-Ala was demonstrated.",

keywords = "Antibiotics, Bioorganic chemistry, Cyclization, Peptides, Receptors",

author = "Arnusch, \{Christopher J.\} and Pieters, \{Roland J.\}",

year = "2003",

month = aug,

day = "11",

doi = "10.1002/ejoc.200300044",

language = "English",

pages = "3131--3138",

journal = "European Journal of Organic Chemistry",

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publisher = "Wiley-VCH Verlag",

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AU - Arnusch, Christopher J.

AU - Pieters, Roland J.

PY - 2003/8/11

Y1 - 2003/8/11

N2 - A solid phase synthesis of a model system of the DE ring system of vancomycin is described. The synthesis involved biocatalytic resolutions of unnatural amino acids, is compatible with conventional solid phase peptide synthesis and contains as the key step: an on-be.ad SNAr cyclization. Binding of a cyclic peptide to the carboxylate of N-Ac-D-Ala was demonstrated.

AB - A solid phase synthesis of a model system of the DE ring system of vancomycin is described. The synthesis involved biocatalytic resolutions of unnatural amino acids, is compatible with conventional solid phase peptide synthesis and contains as the key step: an on-be.ad SNAr cyclization. Binding of a cyclic peptide to the carboxylate of N-Ac-D-Ala was demonstrated.

KW - Antibiotics

KW - Bioorganic chemistry

KW - Cyclization

KW - Peptides

KW - Receptors

UR - https://www.scopus.com/pages/publications/0041977166

U2 - 10.1002/ejoc.200300044

DO - 10.1002/ejoc.200300044

M3 - Article

AN - SCOPUS:0041977166

SN - 1434-193X

SP - 3131

EP - 3138

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 16

ER -

Solid phase synthesis of vancomycin mimics

Abstract

Keywords

ASJC Scopus subject areas

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