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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. https://resolver.caltech.edu/CaltechAUTHORS:20180507-141622455

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Abstract

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.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.1002/(SICI)1521-3773(19981217)37:23<3281::AID-ANIE3281>3.0.CO;2-VDOIArticle
ORCID:
AuthorORCID
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.
Funders:
Funding AgencyGrant Number
NIHUNSPECIFIED
Zeneca PharmaceuticalsUNSPECIFIED
American Chemical SocietyUNSPECIFIED
Subject Keywords:Carbene complexes; Helical structures; Macrocycles; Metathesis; Peptides
Issue or Number:23
Record Number:CaltechAUTHORS:20180507-141622455
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20180507-141622455
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
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:07 May 2018 21:52
Last Modified:03 Oct 2019 19:41

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