Synthesis and Properties of a Sterically Unencumbered δ-Silanediol Amino Acid
- 15 February 2012
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 77 (6), 2901-2906
- https://doi.org/10.1021/jo300175t
Abstract
An amino acid carrying a 1-(4-dihydroxymethylsilyl)butyl side chain has been prepared in enantiomerically pure form as a potential inhibitor of the enzyme arginase, a pharmaceutical target. As a water-soluble silanediol, this compound was anticipated to be entropically stabilized against polymerization and siloxane formation. At 50 mM in D2O, the degree of oligomerization was found to be pH dependent, with diastereomeric mixtures formed on condensation. Above pH 11 the silane is largely monomeric.Keywords
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