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Synthese von Humaninsulin. III. Aufbau des geschützten zweikettigen Fragments A(14‐21) ‐ B(17‐30)
Author(s) -
Kamber Bruno,
Riniker Bernhard,
Sieber Peter,
Rittel Werner
Publication year - 1976
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.19760590821
Subject(s) - chemistry , stereochemistry , fragment (logic) , disulfide bond , sequence (biology) , peptide , azide , biochemistry , organic chemistry , computer science , programming language
Synthesis of human insulin. III. Preparation of the A(14‐21) ‐ B(17‐30) fragment. In the recently published total synthesis of human insulin [1], one of the three principal intermediates is the protected fragment in which sequence 14‐21 of the A chain is linked to sequence 17‐30 of the B chain by the disulfide bridge between A 20 and B 19. The synthesis of this fragment, and its characterization are described in detail in the present report. This open‐chain asymmetrical cystine peptide was prepared by elongating the two chains in the already published intermediate first with fragment A(14–19), Bpoc‐Tyr(Bu t )‐Gln‐Leu‐Glu(OBu t )‐Asn‐Tyr(Bu t )‐NH‐NH 2 (azide coupling), and secondly with fragment B(21–30), H‐Glu(OBu t )‐Arg‐Gly‐Phe‐Phe‐Tyr(Bu t )‐Thr(Bu t )‐Pro‐Lys(Boc)‐Thr(Bu t )‐OBu t (DCCI/HOBt).