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Title: Design and synthesis of amidine-type peptide bond isosteres: application of nitrile oxide derivatives as active ester equivalents in peptide and peptidomimetics synthesis.
Authors: Inokuchi, Eriko
Yamada, Ai
Hozumi, Kentaro
Tomita, Kenji
Oishi, Shinya  kyouindb  KAKEN_id
Ohno, Hiroaki  kyouindb  KAKEN_id
Nomizu, Motoyoshi
Fujii, Nobutaka  KAKEN_id
Author's alias: 大石, 真也
藤井, 信孝
Issue Date: 7-May-2011
Publisher: Royal Society of Chemistry
Journal title: Organic & biomolecular chemistry
Volume: 9
Issue: 9
Start page: 3421
End page: 3427
Abstract: Amidine-type peptide bond isosteres were designed based on the substitution of the peptide bond carbonyl (C=O) group with an imino (C=NH) group. The positively-charged property of the isosteric part resembles a reduced amide-type peptidomimetic. The peptidyl amidine units were synthesized by the reduction of a key amidoxime (N-hydroxyamidine) precursor, which was prepared from nitrile oxide components as an aminoacyl or peptidyl equivalent. This nitrile oxide-mediated C-N bond formation was also used for peptide macrocyclization, in which the amidoxime group was converted to peptide bonds under mild acidic conditions. Syntheses of the cyclic RGD peptide and a peptidomimetic using both approaches, and their inhibitory activity against integrin-mediated cell attachment, are presented.
Rights: © The Royal Society of Chemistry 2011
This is not the published version. Please cite only the published version. この論文は出版社版でありません。引用の際には出版社版をご確認ご利用ください。
DOI(Published Version): 10.1039/c0ob01193b
PubMed ID: 21423919
Appears in Collections:Journal Articles

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