We found a match
Your institution may have access to this item. Find your institution then sign in to continue.
- Title
Synthese von Humaninsulin. II. Aufbau des cyclischen Fragments A(1-13).
- Authors
Sieber, Peter; Kamber, Bruno; Eisler, Karel; Hartmann, Albert; Riniker, Bernhard; Rittel, Werner
- Abstract
Synthesis of human insulin. II. Preparation of the A(1-13) fragment. The present report gives a detailed account of the synthesis of the protected tridecapeptide A(1-13), BocGlyIleValGlu(OBu t)Gln Ser(Bu t)LeuOH ( 20), an essential intermediate in the recently published total synthesis of human insulin [1]. The main feature in the synthesis of 20 was the specific formation of a disulfide bond between A6 and A11 in the presence of an additional cysteine residue (A7). The selective ring closure was accomplished with the segment A(6-13), HCys(Trt)Cys(Acm)Thr(Bu t)Ser(Bu t)IleCys(Trt)Ser(Bu t)LeuOH ( 18), which was obtained by way of conventional synthesis routes. Treatment of 18 with iodine in trifluoroethanol formed the desired disulfide bridge from the two S-trityl-cysteine residues without affecting the S-acetamidomethyl-protected cysteine A7. A final azide coupling with the N-terminal derivative A(1-5) ( 3) provided the tridecapeptide fragment 20 as a crystalline compound.
- Publication
Helvetica Chimica Acta, 1976, Vol 59, Issue 5, p1489
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.19760590510