Synthesis of tripeptides as potent Yersinia protein tyrosine phosphatase inhibitors = 여시니아 프로틴포스포타제 저해기능을 갖는 트리펩타이드 합성

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Title
Synthesis of tripeptides as potent Yersinia protein tyrosine phosphatase inhibitors = 여시니아 프로틴포스포타제 저해기능을 갖는 트리펩타이드 합성
Author(s)
Kyeong Lee; S K Boovanahalli; K Y Nam; S U Kang; MiJeoung Lee; J Phan; L Wu; D S Waugh; Z Y Zhang; K T No; Jung Joon Lee; T R Burke
Bibliographic Citation
Bioorganic & Medicinal Chemistry Letters, vol. 15, no. 18, pp. 4037-4042
Publication Year
2005
Abstract
We report the synthesis of a series of monoanionic phosphotyrosyl (pTyr) mimetic-containing tripeptides based on 'Fmoc-Glu(OBn)-Xxx-Leu-amide' (where Xxx = pTyr mimetic) and their N-terminally modified derivatives. The inhibitory potencies of compounds were tested against YopH and human PTP1B enzymes. Several compounds exhibited noteworthy activity against both YopH and PTP1B. Among the N-terminally modified analogues, 5-methylindole derivative 30 was found to be the best moiety to replace base-labile Fmoc group. A mode of binding with YopH is proposed for tripeptides 21, 30, and 31.
Keyword
bioterrorismPTP1BpTyr mimeticstripeptidesYopH
ISSN
0960-894X
Publisher
Elsevier
DOI
http://dx.doi.org/10.1016/j.bmcl.2005.06.027
Type
Article
Appears in Collections:
1. Journal Articles > Journal Articles
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