Solid‐phase synthesis of chicken vasoactive intestinal peptide by a mild procedure using Nα‐9‐fluorenylmethyloxycarbonyl amino acids
- 12 January 1982
- journal article
- research article
- Published by Wiley in International Journal of Peptide and Protein Research
- Vol. 19 (1) , 71-78
- https://doi.org/10.1111/j.1399-3011.1982.tb03025.x
Abstract
The octacosapeptide amide corresponding to the entire amino acid sequence of chicken vasoactive peptide (VIP) was assembled on a p-benzyloxybenzylamine resin support using the base-labile 9-fluorenylmethyloxycarbonyl as N.alpha.-protecting group, cleaved by mild acid treatment, and purified by gel-filtration and ion exchange chromatography. The symmetrical anhydride coupling was employed and monitored by 2 independent methods, and acetic anhydride termination was incorporated to minimize formation of deletion peptides. The homogeneity of the final product, obtained in 18% yield, was assessed by TLC, disc electrophoresis, amino-terminal amino acid analysis, and amino analyses of acid and enzyme hydrolysates. The purified chicken VIP was active on gastric acid secretion and on pancreatic blood flow. Previously reported ring closure of the Asp-Asn unit seemed to be at a minimum, owing to the mild basic and acid treatments.Keywords
This publication has 47 references indexed in Scilit:
- A new solid-phase synthesis of thymopoietin II by a mild procedureCellular and Molecular Life Sciences, 1981
- STUDIES ON PEPTIDESInternational Journal of Peptide and Protein Research, 1980
- Behaviour of S-substituted cysteine sulfoxide under acidolytical deprotecting conditions.CHEMICAL & PHARMACEUTICAL BULLETIN, 1979
- SIDE REACTIONS IN PEPTIDE SYNTHESISInternational Journal of Peptide and Protein Research, 1978
- Structure of the vasoactive intestinal octacosapeptide from chicken intestine. The amino acid sequenceFEBS Letters, 1975
- Rearrangement of α to β-Aspartyl Peptide with Anhydrous Hydrogen FluorideCHEMICAL & PHARMACEUTICAL BULLETIN, 1973
- Phenyl esters for C-terminal protection in peptide synthesisJournal of the American Chemical Society, 1972
- Specific cleavage of C-methionyl peptide bonds in hydrogen fluorideBiochemical and Biophysical Research Communications, 1964
- Solid Phase Peptide Synthesis. I. The Synthesis of a TetrapeptideJournal of the American Chemical Society, 1963
- An Approach to the Specific Cleavage of Peptide Bonds. I. The Acyl Migration in Dipeptides Containing Hydroxyamino Acids in Anhydrous Hydrogen FluorideJournal of the American Chemical Society, 1962