Abstract
Reduction of carboxyl groups in lysozyme and myoglobin was investigated employing two alkylboranes with differing degrees of steric requirements with the aim of achieving steric control of the direction of hydroboration. Disiamylborane, a dialkylborane with large steric requirements, enabled the specific reduction of accessible glutamic acids and unhindered end-chain carboxyl groups. On the other hand, 9-borabicyclo[3,3,1]nonane, a bicyclic dialkylborane with appreciable hindrance, exhibited good selectivity for glutamate and unhindered C-terminal carboxylate groups with only marginal reduction of β-carboxyl groups of aspartic acid. In addition to their usefulness in specific chemical modification, these reagents may also prove to be valuable conformational probes.
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