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Epsilon substituted lysinol derivatives as HIV-1 protease inhibitors

✍ Scribed by Kristen L.G. Jones; M. Katharine Holloway; Hua-Poo Su; Steven S. Carroll; Christine Burlein; Sinoeun Touch; Daniel J. DiStefano; Rosa I. Sanchez; Theresa M. Williams; Joseph P. Vacca; Craig A. Coburn

Publisher: Elsevier Science
Year: 2010
Tongue: English
Weight: 714 KB
Volume: 20
Category: Article
ISSN: 0960-894X
DOI: 10.1016/j.bmcl.2010.05.082

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✦ Synopsis

A series of HIV-1 protease inhibitors containing an epsilon substituted lysinol backbone was synthesized. Two novel synthetic routes using N-boc-L-glutamic acid alpha-benzyl ester and 2,6-diaminopimelic acid were developed. Incorporation of this epsilon substituent enabled access to the S2 pocket of the enzyme, affording high potency inhibitors. Modeling studies and synthetic efforts suggest the potency increase is due to both conformational bias and van der Waals interactions with the S2 pocket.

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