Premium
Reduction of Insulin with Tributylphosphine
Author(s) -
Rüegg U. Th.,
Rudinger J.
Publication year - 1974
Publication title -
israel journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.908
H-Index - 54
eISSN - 1869-5868
pISSN - 0021-2148
DOI - 10.1002/ijch.197400031
Subject(s) - tributylphosphine , chemistry , yield (engineering) , aqueous solution , imine , medicinal chemistry , insulin , methanol , inorganic chemistry , catalysis , organic chemistry , materials science , metallurgy , medicine , endocrinology
Treatment of bovine insulin with 3 mole of tributylphosphine in the presence of excess ethylene imine in aqueous 1‐propanol at pH 8.2 leads to complete reduction and aminoethylation, affording the aminoethylated insulin A and B chains in excellent yield. Reduction with 1 mole of tributylphosphine under the same conditions is attended by disulphide exchange: The product is a mixture of partially reduced and aminoethylated species which, on further reduction and carboxymethylation, afford A‐ and B‐chain derivatives with varying ratios of S‐aminoethyl‐ and S‐carboxymethyl substituents.