Reactivity of consecutive basic amino acid residues in peptides
- 1 March 1987
- journal article
- research article
- Published by Wiley in International Journal of Peptide and Protein Research
- Vol. 29 (3), 392-405
- https://doi.org/10.1111/j.1399-3011.1987.tb02266.x
Abstract
Different tetrapeptides of general formula L-Ala-X-X-Gly, possessing a basic doublet in the second and third position (X = Arg or Lys), have been synthesized as free or N-acetylated molecules. The chemical reactivity of the arginine guanidino group and of the lysine e-amino group were studied using respectively the Sakaguchi and the orthodiacetylbenzene reactions, in the tetrapeptides as well as in related molecules. In both cases, the colour yield is markedly influenced by the length of the polypeptide chain and by the relative positions of the arginine and lysine residues, suggesting the occurrence of intramolecular bonds within the tetrapeptide molecule. Tryptic hydrolysis of the tetrapeptides was followed by evaluating the amino acids or peptides which appear to be specific for the different possible cleavages at the arginyl or at the lysyl bonds. The susceptibility to trypsin of the carboxylic group of the second basic amino acid decreases progressively in the order Lys-Arg > Arg–Arg ± Lys–Lys > Arg–Lys, which shows a fair correlation with the intra-cellular cleavage of the bonds observed during the processing of preproteins or of the precursors of several physiologically active peptides.Keywords
This publication has 48 references indexed in Scilit:
- Studies on β‐turn of peptidesInternational Journal of Peptide and Protein Research, 1984
- Purification and complete amino acid sequence of α-human atrial natriuretic polypeptide (α-hANP)Biochemical and Biophysical Research Communications, 1984
- The amino acid sequence of an atrial peptide with potent diuretic and natriuretic propertiesBiochemical and Biophysical Research Communications, 1983
- α-Neo-endorphin: A “big” leu-enkephalin with potent opiate activity from porcine hypothalamiBiochemical and Biophysical Research Communications, 1979
- SYNTHESIS and PROPERTIES OF ARGININE OLIGOPEPTIDESInternational Journal of Protein Research, 1970
- Use of Ilydrogen Fluoride in Merrifield Solid-Phase Peptide SynthesisJournal of the American Chemical Society, 1967
- Substances showing color reaction with o-diacetylbenzeneBUNSEKI KAGAKU, 1967
- Solid Phase Peptide Synthesis. I. The Synthesis of a TetrapeptideJournal of the American Chemical Society, 1963
- A New Method of Forming Peptide BondsJournal of the American Chemical Society, 1955
- Über das 1.2‐Diacetyl‐benzolEuropean Journal of Inorganic Chemistry, 1948