Fast and versatile microwave-assisted intramolecular Heck reaction in peptide macrocyclization using microwave energy
We have revisited the intramolecular Heck reaction and investigated the microwave‐assisted macrocyclization on preformed peptides using a model series of ring‐varying peptides acryloyl‐Gly‐[Gly]n‐Phe(4‐I)NHR; n 0–4. The method was applied to both solution and solid supported cyclizations. We demon...
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Published in | Biopolymers Vol. 84; no. 3; pp. 274 - 282 |
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Main Authors | , , |
Format | Journal Article |
Language | English |
Published |
Hoboken
Wiley Subscription Services, Inc., A Wiley Company
2006
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Subjects | |
Online Access | Get full text |
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Summary: | We have revisited the intramolecular Heck reaction and investigated the microwave‐assisted macrocyclization on preformed peptides using a model series of ring‐varying peptides acryloyl‐Gly‐[Gly]n‐Phe(4‐I)NHR; n 0–4. The method was applied to both solution and solid supported cyclizations. We demonstrate that the intramolecular Heck reaction can be performed in peptides both in solution and solid support using a modified domestic microwave within 1 to 30 minutes in DMF under reflux with moderate yields ranging from 15 to 25% for a scale between 2–45 mg of linear precursors. The approach was applied to the synthesis of a constrained biologically relevant peptidomimetic bearing an Arg‐Gly‐Asp (RGD) sequence. These results make the microwave‐assisted Heck reaction an attractive renovated approach for peptidomimetics. © 2005 Wiley Periodicals, Inc. Biopolymers (Pept Sci) 84: 274–282, 2006
This article was originally published online as an accepted preprint. The “Published Online” date corresponds to the preprint version. You can request a copy of the preprint by emailing the Biopolymers editorial office at biopolymers@wiley.com |
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Bibliography: | ark:/67375/WNG-5R2M8QNZ-7 istex:19A469BD5267FC3ED3DEE2009E682E457E8E1ADA ArticleID:BIP20411 U.S.-Israel Bi-National Science Foundation - No. 1998378 ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 ObjectType-Article-2 ObjectType-Feature-1 |
ISSN: | 0006-3525 1097-0282 |
DOI: | 10.1002/bip.20411 |