Synthese von Humaninsulin. III. Aufbau des geschützten zweikettigen Fragments A(14-21) - B(17-30)
✍ Scribed by Bruno Kamber; Bernhard Riniker; Peter Sieber; Werner Rittel
- Publisher
- John Wiley and Sons
- Year
- 1976
- Tongue
- German
- Weight
- 701 KB
- Volume
- 59
- Category
- Article
- ISSN
- 0018-019X
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✦ Synopsis
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).