Reduction of Insulin with Tributylphosphine | Zendy

Rüegg U. Th. | Zendy; Rudinger J. | Zendy

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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.

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