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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Bibliographic Details
Published inBiopolymers Vol. 84; no. 3; pp. 274 - 282
Main Authors Byk, Gerardo, Cohen-Ohana, Mirit, Raichman, Daniel
Format Journal Article
LanguageEnglish
Published Hoboken Wiley Subscription Services, Inc., A Wiley Company 2006
Subjects
Amino Acid Sequence
Amino Acids - chemistry
Chromatography, High Pressure Liquid
Dimerization
Dimethylformamide - chemistry
Heck macrocyclization
Kinetics
Magnetic Resonance Spectroscopy
Mass Spectrometry
microwave energy
Microwaves
Molecular Weight
Oligopeptides - chemistry
Peptides, Cyclic - chemical synthesis
Peptides, Cyclic - chemistry
Peptides, Cyclic - radiation effects
peptidomimetics
Protein Conformation
RGD sequence
Solutions
Structure-Activity Relationship
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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
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
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ISSN:0006-3525
1097-0282
DOI:10.1002/bip.20411