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Thyrocalcitonin IV. Die Totalsynthese des α‐Thyrocalcitonins
Author(s) -
Riniker B.,
Brugger M.,
Kamber B.,
Sieber P.,
Rittel W.
Publication year - 1969
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19690520420
Subject(s) - chemistry , disulfide bond , stereochemistry , total synthesis , cysteine , peptide , peptide synthesis , biochemistry , enzyme
The total synthesis of the hypocalcaemic hormone α‐thyrocalcitonin (I) isolated from porcine thyroid glands is reported in detail. By the fragment condensation approach, using coupling procedures known to avoid racemisation, the fully protected dotriacontapeptide sequence II was synthesised. In the build up of II the disulfide ring bridge connecting the cysteine residues 1 and 7 was preformed in the protected nonapeptide fragment 1–9. Simultaneous removal by acidolysis of the nine protecting groups present in II yielded synthetic α‐thyrocalcitonin (I) in a state of high purity and possessing full biological activity; the disulfide bond remained intact during the de‐protection step. On repeated biological assay the synthetic preparation I in the test system of K UMAR et al. [2] was found to possess an activity of 130.8 U/mg peptide.