Synthesis of Amino Acid-Derived Cyclic Acyl Amidines for Use in -Strand Peptidomimetics

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• 作者：Ming C. Hammond ; Paul A. Bartlett
• 刊名：Journal of Organic Chemistry
• 出版年：2007
• 出版时间：April 13, 2007
• 年：2007
• 卷：72
• 期：8
• 页码：3104 - 3107
• 全文大小：156K
• 年卷期：v.72,no.8(April 13, 2007)
• ISSN：1520-6904

文摘

The acyl amidine represented by the 4,5-dihydro-2(3H)-pyrazinone ring system 2 is isosteric to the vinylogous amideof the 1,2-dihydro-3(6H)-pyridinone 1, but its assembly fromseparate amine and amide components enables ready incorporation of an amino acid side chain with correct regio- andstereochemistry. -Strand peptidomimetics incorporatingamino acid analogues based on 2 have recently been shownto be potent, protease-resistant ligands to a PDZ protein-interaction domain. Two routes to the protected dipeptideanalogue 3 are described.