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Impact of the central hydroxyl groups on the activity of symmetrical HIV-1 protease inhibitors derived from L-mannaric acid
Department of Organic Chemistry, Arrhenius Lab., Stockholm Univ., S., Stockholm, Sweden.
Mühlman, A., Department of Organic Chemistry, Arrhenius Lab., Stockholm Univ., S., Stockholm, Sweden.
Department of Organic Chemistry, Arrhenius Lab., Stockholm Univ., S., Stockholm, Sweden.
Linköping University, The Institute of Technology. Linköping University, Department of Physics, Chemistry and Biology, Organic Chemistry .
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2000 (English)In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 56, no 20, 3219-3225 p.Article in journal (Refereed) Published
Abstract [en]

The influence of the central hydroxyl groups on the anti-viral activity of symmetrical HIV-1 protease inhibitors derived from L-mannaric acid has been examined. L-Iditol was synthesized and used as a chiral precursor for the synthesis of the corresponding inhibitor with inverted configuration at C-3 and C-4. Key intermediates were 3,4-O-isopropylidene-L-iditol and the activated L-idaric acid succinimidyI ester. The configurations of the central hydroxyl groups required for optimal inhibition of the HIV-1 protease were determined to be the C-3R and C-4R, i.e. the L-manno-configuration. Three C2-symmetric inhibitors were converted to their thiocarbonates and reduced to provide the corresponding hydroxyethyl transition-state mimics. Deletion of the C-4 hydroxyl group in these inhibitors gave no further improvement in the anti-viral activity. (C) 2000 Published by Elsevier Science Ltd.

Place, publisher, year, edition, pages
2000. Vol. 56, no 20, 3219-3225 p.
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Engineering and Technology
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URN: urn:nbn:se:liu:diva-47651DOI: 10.1016/S0040-4020(00)00220-9OAI: oai:DiVA.org:liu-47651DiVA: diva2:268547
Available from: 2009-10-11 Created: 2009-10-11 Last updated: 2017-12-13

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Kvarnström, Ingemar

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