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

20 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

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10.1002/ejoc.200300044

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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.",

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year = "2003",

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AU - Pieters, Roland J.

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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.

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KW - Bioorganic chemistry

KW - Cyclization

KW - Peptides

KW - Receptors

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SN - 0365-5490

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Solid phase synthesis of vancomycin mimics

Abstract

Keywords

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