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New segment synthesis of α-inhibin-92 by the acyl disulfide method
| Content Provider | Scilit |
|---|---|
| Author | Yamashiro, Donald Li, Choh Hao |
| Copyright Year | 1988 |
| Description | Journal: International journal of peptide and protein research The thiocarboxyl group reacts with diaryl disulfides to give an unsymmetrical acyl disulfide in dimethylformamide (DMF) and a symmetrical diacyl disulfide in aqueous DMF. Both acyl disulfides react with the α-amino group to form the peptide bond. The method was used in a new segment synthesis of α-inhibin-92 (α-IB-92) with use of 2,2′-dipyridyl disulfide as activator. Thiocarboxyl peptides were synthesized by the solid-phase method on 4-[α-(Boc-Gly-S)benzyl]phenoxyacetamidomethyl-resin. The segments α-IB-92-(1–34)SH (I), Msc-α-IB-92-(35–65)SH (II), Msc-α-IB-92(66–92)OH (III), and Msc-α-IB-92-(35–92)OH (VI) were prepared in yields of 33, 36, 41, and 25%, respectively, with use of crystalline symmetrical anhydrides in double and triple coupling protocols. Segments I, II, and III were used in a 3-segment synthesis of α-IB-92 with an overall yield based on starting resin of about 8% while a 2-segment synthesis using I and IV gave 11%. An all stepwise synthesis of α-IB-92 gave 4.5%. |
| Related Links | https://onlinelibrary.wiley.com/doi/pdf/10.1111/j.1399-3011.1988.tb00040.x |
| Ending Page | 334 |
| Page Count | 13 |
| Starting Page | 322 |
| ISSN | 03678377 |
| DOI | 10.1111/j.1399-3011.1988.tb00040.x |
| Journal | International journal of peptide and protein research |
| Issue Number | 3 |
| Volume Number | 31 |
| Language | English |
| Publisher | Wiley-Blackwell |
| Publisher Date | 1988-03-01 |
| Access Restriction | Open |
| Subject Keyword | Journal: International journal of peptide and protein research Crystalline Symmetrical Anhydrides 2.2′-dipyridyl Disulfide Solid-phase Peptide Synthesis |
| Content Type | Text |
| Resource Type | Article |
| Subject | Biochemistry |
