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Process for producing an insulin precursor
| Details |
Inventors: Frank, Bruce H.;
Assignee: Eli Lilly and Company (Indianapolis, IN)
Primary Examiner: Waddell; Frederick E.
Assistant Examiner:
Attorney, Agent or Firm: Martens, Jr.; William C., Whale; Arthur R.
A proinsulin-like disulfide insulin precursor is produced from its corresponding linear chain S-sulfonate insulin precursor by reacting the S-sulfonate with a mercaptan in an amount which provides from about 1 to about 5 --SH moieties per --SSO.sub.3.sup.- moiety in an aqueous medium at a pH of from about 7 to about 11.5 and at an S-sulfonate concentration of up to about 10 mg. per ml. of aqueous medium. |
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DETAILED DESCRIPTION OF THE INVENTION As indicated, this invention is directed to a process for producing an insulin precursor.
As used herein, the term "insulin precursor" refers to a molecule which (1) contains an insulin A-chain and an insulin B-chain, (2) has at least three disulfide bonds represented by a joining of the sulfurs of each of the Cys moieties located in the A- and B-chains at (a) A-6 and A-11, (b) A-7 and B-7, and (c) A-20 and B-19, respectively, and (3) has a removable connecting moiety which is joined to the insulin A-chain at the amino group of A-1 and to the insulin B-chain at the .
epsilon.
-amino group of the lysine residue at B-29 or the carboxyl group of the amino acid residue at B-30.
The group Z, which defines the B-30 amino acid residue of insulin, is any of Ala, Thr, or Ser.
These residues represent naturally occurring insulins, Thr in human insulin, Ala in bovine and porcine insulins, and Ser in rabbit insulin.
The group R is hydrogen, and amino acid residue, or a peptide moiety having at least two amino acid residues.
In those instances in which R is an amino acid residue or a peptide moiety, R is a group which is cleavable from the insulin precursor product of the process of this invention without loss of the integrity of the residual insulin structure.
Any of a wide variety of amino acid residues of peptide moieties qualify within the definition of the group R.
Examples of cleavable amino acid residues are basic amino acids such as arginine (Arg) or lysine (Lys) as well as peptide moieties terminating at the carboxyl by such amino acid residues.
These are recognized as susceptible to cleavage upon treatment with the proteolytic enzyme trypsin.
Another example of a cleavable amino acid residue is methionine (Met) as well, again, as a peptide moiety having Met at its carboxy terminal.
These can be removed by treatment with cyanogen bromide.
A further example is tryptophan (Trp) or a peptide moiety containing Trp at its carboxy terminal.
This is removed upon treatment with N-bromosuccinimide
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