Synthesis of tripeptides as potent Yersinia protein tyrosine phosphatase inhibitors

Kyeong Lee; Shanthaveerappa K. Boovanahalli; Ky Youb Nam; Sang Uk Kang; Mijeoung Lee; Jason Phan; Li Wu; David S. Waugh; Zhong Yin Zhang; Tai No Kyoung; Jun Lee Jung; Terrence R. Burke

doi:10.1016/j.bmcl.2005.06.027

Synthesis of tripeptides as potent Yersinia protein tyrosine phosphatase inhibitors

Kyeong Lee, Shanthaveerappa K. Boovanahalli, Ky Youb Nam, Sang Uk Kang, Mijeoung Lee, Jason Phan, Li Wu, David S. Waugh, Zhong Yin Zhang, Tai No Kyoung, Jun Lee Jung, Terrence R. Burke

Research output: Contribution to journal › Article

19 Citations (Scopus)

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.

Original language	English
Pages (from-to)	4037-4042
Number of pages	6
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	15
Issue number	18
DOIs	https://doi.org/10.1016/j.bmcl.2005.06.027
Publication status	Published - 2005 Sep 15

All Science Journal Classification (ASJC) codes

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

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Lee, K., Boovanahalli, S. K., Nam, K. Y., Kang, S. U., Lee, M., Phan, J., Wu, L., Waugh, D. S., Zhang, Z. Y., Kyoung, T. N., Jung, J. L., & Burke, T. R. (2005). Synthesis of tripeptides as potent Yersinia protein tyrosine phosphatase inhibitors. Bioorganic and Medicinal Chemistry Letters, 15(18), 4037-4042. https://doi.org/10.1016/j.bmcl.2005.06.027

Lee, Kyeong ; Boovanahalli, Shanthaveerappa K. ; Nam, Ky Youb ; Kang, Sang Uk ; Lee, Mijeoung ; Phan, Jason ; Wu, Li ; Waugh, David S. ; Zhang, Zhong Yin ; Kyoung, Tai No ; Jung, Jun Lee ; Burke, Terrence R. / Synthesis of tripeptides as potent Yersinia protein tyrosine phosphatase inhibitors. In: Bioorganic and Medicinal Chemistry Letters. 2005 ; Vol. 15, No. 18. pp. 4037-4042.

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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.",

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Synthesis of tripeptides as potent Yersinia protein tyrosine phosphatase inhibitors. / Lee, Kyeong; Boovanahalli, Shanthaveerappa K.; Nam, Ky Youb; Kang, Sang Uk; Lee, Mijeoung; Phan, Jason; Wu, Li; Waugh, David S.; Zhang, Zhong Yin; Kyoung, Tai No; Jung, Jun Lee; Burke, Terrence R.

In: Bioorganic and Medicinal Chemistry Letters, Vol. 15, No. 18, 15.09.2005, p. 4037-4042.

Research output: Contribution to journal › Article

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AU - Lee, Kyeong

AU - Boovanahalli, Shanthaveerappa K.

AU - Nam, Ky Youb

AU - Kang, Sang Uk

AU - Lee, Mijeoung

AU - Phan, Jason

AU - Wu, Li

AU - Waugh, David S.

AU - Zhang, Zhong Yin

AU - Kyoung, Tai No

AU - Jung, Jun Lee

AU - Burke, Terrence R.

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