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^*

^*Corresponding author for this work

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

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-bead SNAr 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
Volume	2003
Issue number	16
DOIs	https://doi.org/10.1002/ejoc.200300044
Publication status	Published - 2003

Keywords

Antibiotics
Bioorganic chemistry
Cyclization
Peptides
Receptors

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10.1002/ejoc.200300044

Eur J Org Chem - 2003 - Arnusch - Solid Phase Synthesis of Vancomycin MimicsFinal published version, 170 KBLicence: Taverne

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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-bead 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",

doi = "10.1002/ejoc.200300044",

language = "English",

volume = "2003",

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journal = "European Journal of Organic Chemistry",

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T1 - Solid phase synthesis of Vancomycin mimics

AU - Arnusch, Christopher J.

AU - Pieters, Roland J.

PY - 2003

Y1 - 2003

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-bead 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-bead 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

SN - 1434-193X

VL - 2003

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

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