Possible involvement of the A/sup 20/-A/sup 21/ peptide bond in the expression of the biological activity of insulin. 1. (21-Desasparagine,20-cysteinamide-A)insulin and (21-desasparagine,20-cysteine isopropylamide-A)insulin

Journal Article · Tue Nov 03 00:00:00 EST 1987 · Biochemistry; (United States)

OSTI ID:5599753

Chu, Y C; Wang, R Y; Burke, G T; Chanley, J D; Katsoyannis, P G

The C-terminal region of the A chain of insulin has been shown to play a significant role in the expression of the biological activity of the hormone. To further delineate the contribution of this segment, we have synthesized (21-desasparagine,20-cysteinamide-A)insulin and (21-desasparagine,20-cysteine isopropylamide-A)insulin, in which the C-terminal amino acid residue of the A chain of insulin, asparagine, has been removed and the resulting free carboxyl group of the A/sup 20/ cysteine residue has been converted to an amide and an isopropylamide, respectively. Both insulin analogues display biological activity, 14-15% for the unsubstituted amide analogue and 20-22% for the isopropylamide analogue, both relative to bovine insulin. In contrast, a (21-desasparagine-A)insulin analogue has been reported to display less than 4% of the activity of the natural hormone. The implications of these findings are discussed, and we conclude that the A/sup 20/-A/sup 21/ amide bond plays a significant role in the expression of the biological activity of insulin.

• Research Organization: City Univ. of New York, NY
• OSTI ID: 5599753
• Journal Information: Biochemistry; (United States), Vol. 26:22
• Country of Publication: United States
• Language: English

Related Subjects

62 RADIOLOGY AND NUCLEAR MEDICINE
CELL MEMBRANES
CONFIGURATION INTERACTION
INSULIN
BIOSYNTHESIS
DERIVATIZATION
RADIOIMMUNOASSAY
CHEMICAL BONDS
IODINE 125
LIVER
RATS
ANIMALS
BETA DECAY RADIOISOTOPES
BODY
CELL CONSTITUENTS
CHEMICAL REACTIONS
DAYS LIVING RADIOISOTOPES
DIGESTIVE SYSTEM
ELECTRON CAPTURE RADIOISOTOPES
GLANDS
HORMONES
IMMUNOASSAY
IMMUNOLOGY
INTERMEDIATE MASS NUCLEI
IODINE ISOTOPES
ISOTOPE APPLICATIONS
ISOTOPES
MAMMALS
MEMBRANES
NUCLEI
ODD-EVEN NUCLEI
ORGANS
PEPTIDE HORMONES
RADIOASSAY
RADIOIMMUNOLOGY
RADIOISOTOPES
RODENTS
SYNTHESIS
TRACER TECHNIQUES
VERTEBRATES
550601* - Medicine- Unsealed Radionuclides in Diagnostics