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 | |
| Publication status | Published - 2005 Sep 15 |
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All Science Journal Classification (ASJC) codes
- Biochemistry
- Molecular Medicine
- Molecular Biology
- Pharmaceutical Science
- Drug Discovery
- Clinical Biochemistry
- Organic Chemistry
Cite this
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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
TY - JOUR
T1 - Synthesis of tripeptides as potent Yersinia protein tyrosine phosphatase inhibitors
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.
PY - 2005/9/15
Y1 - 2005/9/15
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=23644432990&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=23644432990&partnerID=8YFLogxK
U2 - 10.1016/j.bmcl.2005.06.027
DO - 10.1016/j.bmcl.2005.06.027
M3 - Article
C2 - 16039123
AN - SCOPUS:23644432990
VL - 15
SP - 4037
EP - 4042
JO - Bioorganic and Medicinal Chemistry Letters
JF - Bioorganic and Medicinal Chemistry Letters
SN - 0960-894X
IS - 18
ER -