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Highly Efficient Synthesis of Covalently Cross-Linked Peptide Helices by Ring-Closing Metathesis

Blackwell, Helen E. and Grubbs, Robert H. (1998) Highly Efficient Synthesis of Covalently Cross-Linked Peptide Helices by Ring-Closing Metathesis. Angewandte Chemie International Edition, 37 (23). pp. 3281-3284. ISSN 1433-7851. doi:10.1002/(SICI)1521-3773(19981217)37:23<3281::AID-ANIE3281>3.0.CO;2-V.

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Olefin metathesis has been successfully applied to the synthesis of macrocyclic helical peptides [Eq. (a)]. Carbon–carbon bond tethers between amino acid side chains were introduced by ring‐closing metathesis. This macrocyclization protocol is a novel and mild procedure for introducing nonnative covalent cross‐links into peptide helices.

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URLURL TypeDescription<3281::AID-ANIE3281>3.0.CO;2-VDOIArticle
Grubbs, Robert H.0000-0002-0057-7817
Additional Information:© 1998 Wiley‐VCH Verlag GmbH, Weinheim, Fed. Rep. of Germany. Issue Online: 23 December 1998; Version of Record online: 23 December 1998: Manuscript received: 18 June 1998. Financial support has been generously provided by the National Institutes of Health and Zeneca Pharmaceuticals. H. E. B. is grateful to the ACS Division of Organic Chemistry for a pre-doctoral fellowship (supported by Pfizer, Inc.). We thank Dr. Keith Russell (Zeneca) for instrumental discussions and Dr. Saeed Khan (UCLA) for X-ray crystallographic analyses. Dr. Isabella L. Karle, Prof. Barbara Imperiali, Prof. Scott J. Miller, and Prof. Daniel J. O'Leary are acknowledged for helpful discussions.
Funding AgencyGrant Number
Zeneca PharmaceuticalsUNSPECIFIED
American Chemical SocietyUNSPECIFIED
Subject Keywords:Carbene complexes; Helical structures; Macrocycles; Metathesis; Peptides
Issue or Number:23
Record Number:CaltechAUTHORS:20180507-141622455
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Official Citation:Blackwell, H. E. and Grubbs, R. H. (1998), Highly Efficient Synthesis of Covalently Cross‐Linked Peptide Helices by Ring‐Closing Metathesis. Angewandte Chemie International Edition, 37: 3281-3284. doi:10.1002/(SICI)1521-3773(19981217)37:23<3281::AID-ANIE3281>3.0.CO;2-V
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:86267
Deposited By: Tony Diaz
Deposited On:07 May 2018 21:52
Last Modified:15 Nov 2021 20:36

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