Stereoselective Synthesis of 3-Substituted 2-Aminocyclopentanecarboxylic Acid Derivatives and Their Incorporation into Short 12-Helical g src="http://pubs.acs.org/images/gifchars/beta2.gif" border=

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• 作者：Matthew G. Woll ; John D. Fisk ; Paul R. LePlae ; and Samuel H. Gellman
• 刊名：Journal of the American Chemical Society
• 出版年：2002
• 出版时间：October 23, 2002
• 年：2002
• 卷：124
• 期：42
• 页码：12447 - 12452
• 全文大小：141K
• 年卷期：v.124,no.42(October 23, 2002)
• ISSN：1520-5126

文摘

A stereoselective synthetic route is reported for the introduction of side chains at the 3-positionof trans-2-aminocyclopentanecarboxylic acid (ACPC). Ring opening of the aziridine 2-benzyloxymethyl-6-azabicyclo[3.1.0]hexane with selected nucleophiles occurs in a regioselective manner and provides ACPCprecursors with functional groups at the 3-position, trans to the 2-amino group. Oligomers composed ofthe 3-substituted ACPC residues maintain the 12-helical conformation displayed by the nonsubstitutedanalogues, as shown by their similar circular dichroism signatures. The added diversity of the new residuesprovides good dispersion of NMR signals, allowing the assignment of nearly all the NOE signals of a selectedhexamer in aqueous solution. The NOEs between protons on nonadjacent residues are characteristic ofthe 12-helix. 3-Substituted ACPC residues allow one to arrange specific functional groups in a geometricallydefined fashion, which should facilitate the design of ges/gifchars/beta2.gif" BORDER=0 ALIGN="middle">-peptides for biological applications.