Chemical synthesis of urotensin II, a somatostatin‐like peptide in the caudal neurosecretory system of fishes
- 1 May 1982
- journal article
- research article
- Published by Wiley in International Journal of Peptide and Protein Research
- Vol. 19 (5), 448-453
- https://doi.org/10.1111/j.1399-3011.1982.tb02629.x
Abstract
In the goby, Gillichthys mirabilis, urotensin II (a bioactive neuropeptide present in the urophysis of teleost fish) has the dodecapeptide sequence, H2N-AGTADC-FWKYCV-OH, which is homologous with mammalian somatostatin at positions 1, 2 and 7-9. The Merrifield solid phase synthesis of Gillichthys urotensin II (UII) was accomplished by stepwise assembly from the carboxy terminus using N.alpha.-tert.-butyloxycarbonyl amino acids containing benzyl-derived groups for protection of side-chain functionalities. Coupling of amino acids to the growth peptide was mediated by diisopropylcarbodiimide in the presence of 1-hydroxybenzotriazole (HOBt). Residual .alpha.-amino groups remaining after coupling were blocked by acetylation with 1-acetylimidazole. Crude, synthetic UII was extracted from the HF-treated, protected peptide-resin product, reduced with dithiothreitol, reoxidized at high dilution with O2, and separated into its components using a single, preparative, reverse-phase HPLC [high pressure liquid chromatography] step. The pure, synthetic UII, obtained in 7.6% yield from oxidized crude UII, was indistinguishable from pure, native UII in specific bioactivity, amino acid sequence, and retention time in each of 2 different HPLC systems.Keywords
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