Cross-linking reagent for insulin synthesis

Details Cross-linking reagent for insulin synthesis Cross-linking reagent for insulin synthesis

1974-09-03

1976-12-07

Myers, Jane S.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

2603264, 260471A, 260544F, 260544Y, 260546, C07C103147, C07C103183, C07C14920

Patent

active

039962687

ABSTRACT:
Carbonyl-bis (L-methionine p-nitrophenyl ester) and its analogues are useful reagents for the intermolecular cross-linking of two chain peptide molecules such as occur in the hormone insulin. The cross-linking occurs across amino groups at preferred positions in the two peptide chains to fix the relative spacial position of the peptide chains and permit the oxidative formation of necessary disulfide bridges between the chains in high yields. The reagent is then removed from the linked chains to yield the insulin molecule. A method for preparation of the reagent is disclosed. Further, a procedure is disclosed by which the cross-linking reagent is used to specifically block certain amino groups on insulin to yield a cross-linked insulin which in turn is used to prepare isotopically labeled insulin and insulin analogues.

REFERENCES:
patent: 3330857 (1967-07-01), Hess
Fieser et al., Reagents for Organic Synthesis, vol. 1 (1967), pp. 842, 1196.
Bodansky et al., J. Amer. Chem. Soc., vol. 81 (1959), pp. 5688-5691.
Schwartz et al., J. Amer. Chem. Soc., vol. 81 (1959), pp. 5691-5695.

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