SYNTHESIS OF α‐ AND β‐MELANOCYTE STIMULATING HORMONES*
- 1 February 1980
- journal article
- Published by Wiley in International Journal of Peptide and Protein Research
- Vol. 15 (2) , 130-138
- https://doi.org/10.1111/j.1399-3011.1980.tb02559.x
Abstract
The solid phase synthesis of α‐melanocyte stimulating hormone (α‐MSH) using the benzhydrylamine resin and a number of recently described side chain protecting groups is given. The carboxamide terminal peptide was obtained directly by treatment of the peptide resin with liquid hydrogen fluoride at 0 in the presence of carbonium ion scavengers. The solid phase synthesis of the C‐terminal carboxylate hormone, porcine β‐melanocyte stimulating hormone (βp‐MSH), using a 1% cross‐linked Merrifield resin and the same side chain protecting groups as in the α‐MSH synthesis also is presented. Purification of both peptides was carried out by conventional chromatographic techniques. Both hormones were fully active and βp‐MSH was slightly more potent than previously reported in the literature.Keywords
This publication has 25 references indexed in Scilit:
- Synthesis of specific deuterium labeled tyrosine and phenylalanine derivatives and their use in the total synthesis of [8-arginine]vasopressin derivatives: the separation of diastereomeric [8-arginine]vasopressin derivatives by partition chromatographyJournal of the American Chemical Society, 1977
- Synthesis and biological activity of .beta.-melanotropins and analogsJournal of Medicinal Chemistry, 1977
- Synthesis and biological activity of camel and bovine .beta.-melanotropinsJournal of Medicinal Chemistry, 1976
- RE-INTRODUCTION AND EVALUATION OF AN ACCURATE, HIGH CAPACITY BIOASSAY FOR MELANOCYTE-STIMULATING HORMONE USING THE SKIN OF ANOLIS CAROLINENSIS IN VITROJournal of Endocrinology, 1975
- The Preparation of Merrifield‐Resins Through Total Esterification With Cesium SaltsHelvetica Chimica Acta, 1973
- Use of chlorinated benzyloxycarbonyl protecting groups to eliminate N.epsilon.-branching at lysine during solid-phase peptide synthesisJournal of the American Chemical Society, 1973
- Improved Solid-Phase Synthesis of Tryptophan-Containing Peptides. I. Use of Hydrogen Chloride in Formic Acid as a Reagent for the Cleavage of t-Butyloxycarbonyl GroupBulletin of the Chemical Society of Japan, 1972
- Angiotensin II analogs. III. Synthesis and biological evaluation of some des-aspartyl-angiotensinsJournal of Medicinal Chemistry, 1970
- Amino-Acid Sequence of the α-Melanocyte-Stimulating HormoneNature, 1957
- ISOLATION AND STRUCTURE OF MELANOCYTE-STIMULATING HORMONE FROM PORCINE PITUITARY GLANDS1Journal of the American Chemical Society, 1956