Trimethylsilyl Cyanide in Peptide Strategies. Part III. Needlessness for complementary hydroxyl side-chain protection
✍ Scribed by M. J. O. Anteunis; Chr. Becu; F. Becu; R. Callens
- Book ID
- 101761205
- Publisher
- Wiley (John Wiley & Sons)
- Year
- 2010
- Weight
- 199 KB
- Volume
- 96
- Category
- Article
- ISSN
- 0037-9646
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✦ Synopsis
for Asp and Glu) in peptide synthe8es that are mediated by T W -C N , whereby silylesters and ether8 are formed and are stable enough even during activation of carboxylic components. This allows Head-to-Tail elongation strategies and fragment condensations without recourse to additional side-chain protection except for m i n e and amide functionalities. Moreover, stereomutation during the H-t-T preparation of 2-Trp-Ser-Tyr-OH and 2-Ser-Tyr-Gly-OH is almost absent. No extra side-chain protection ie needed for Serf Thr, Tyr and Cys (nor We have recently reported (1) on new reaction conditions for peptide couplings, whereby the amino component is per-silylated with TW-CN, prior to its addition to the activated carboxylic component. The most attractive aspects of this strategy are : il rapid and clean peptidation occurs with activated (&no) acid species without recourse to a base during coupling, thus avoiding the major problem of racemization even in absence of otherwise needed suppressors;