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Fast and versatile microwave‐assisted intramolecular Heck reaction in peptide macrocyclization using microwave energy
Author(s) -
Byk Gerardo,
CohenOhana Mirit,
Raichman Daniel
Publication year - 2005
Publication title -
peptide science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.556
H-Index - 125
eISSN - 1097-0282
pISSN - 0006-3525
DOI - 10.1002/bip.20411
Subject(s) - intramolecular force , peptidomimetic , chemistry , heck reaction , combinatorial chemistry , stille reaction , preprint , microwave , peptide , ring (chemistry) , click chemistry , stereochemistry , organic chemistry , catalysis , palladium , physics , biochemistry , quantum mechanics
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