Synthesis of bicyclic tripeptides inspired by the ABC-ring system of vancomycin through ruthenium-based cyclization chemistries

Xin Yang; Lucas P. Beroske; Johan Kemmink; Dirk T.S. Rijkers; Rob M.J. Liskamp

doi:10.1016/j.tetlet.2017.10.046

Synthesis of bicyclic tripeptides inspired by the ABC-ring system of vancomycin through ruthenium-based cyclization chemistries

Xin Yang, Lucas P. Beroske, Johan Kemmink, Dirk T.S. Rijkers^*, Rob M.J. Liskamp

^*Corresponding author for this work

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

Abstract

The synthesis of a bicyclic tripeptide that mimics the ABC ring system of vancomycin is described by using a ring closing metathesis (RCM) – peptide coupling – ruthenium-catalyzed azide-alkyne cycloaddition (RuAAC) strategy.

Original language	English
Pages (from-to)	4542-4546
Number of pages	5
Journal	Tetrahedron Letters
Volume	58
Issue number	48
DOIs	https://doi.org/10.1016/j.tetlet.2017.10.046
Publication status	Published - 29 Nov 2017

Keywords

Macrocycles
Peptides
Peptidomimetics
Ring-closing metathesis
Ru-based azide-alkyne cycloaddition

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10.1016/j.tetlet.2017.10.046Licence: CC BY-NC-ND

1-s2.0-S0040403917313382-mainFinal published version, 579 KBLicence: CC BY-NC-ND

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title = "Synthesis of bicyclic tripeptides inspired by the ABC-ring system of vancomycin through ruthenium-based cyclization chemistries",

abstract = "The synthesis of a bicyclic tripeptide that mimics the ABC ring system of vancomycin is described by using a ring closing metathesis (RCM) – peptide coupling – ruthenium-catalyzed azide-alkyne cycloaddition (RuAAC) strategy.",

keywords = "Macrocycles, Peptides, Peptidomimetics, Ring-closing metathesis, Ru-based azide-alkyne cycloaddition",

author = "Xin Yang and Beroske, {Lucas P.} and Johan Kemmink and Rijkers, {Dirk T.S.} and Liskamp, {Rob M.J.}",

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AU - Yang, Xin

AU - Beroske, Lucas P.

AU - Kemmink, Johan

AU - Rijkers, Dirk T.S.

AU - Liskamp, Rob M.J.

PY - 2017/11/29

Y1 - 2017/11/29

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AB - The synthesis of a bicyclic tripeptide that mimics the ABC ring system of vancomycin is described by using a ring closing metathesis (RCM) – peptide coupling – ruthenium-catalyzed azide-alkyne cycloaddition (RuAAC) strategy.

KW - Macrocycles

KW - Peptides

KW - Peptidomimetics

KW - Ring-closing metathesis

KW - Ru-based azide-alkyne cycloaddition

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ER -

Synthesis of bicyclic tripeptides inspired by the ABC-ring system of vancomycin through ruthenium-based cyclization chemistries

Abstract

Keywords

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