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Synfacts 2023; 19(12): 1273
DOI: 10.1055/s-0043-1763566
Peptide Chemistry

Thiol-Labile Amino Protecting Group that Suppresses the Epimerization in Peptide Synthesis

Autoren

    Rezensent(en):

  • Hisashi Yamamoto

  • Kazumasa Kon

Zhou Y, Li H, Huang Y, Li J, Deng G, Chen G, Xi Z, Zhou C. * Nankai University, Tianjin, P.R. of China
Suppression of Alpha-Carbon Racemization in Peptide Synthesis Based on a Thiol-Labile Amino Protecting Group.

Nat. Commun. 2023;
14
DOI: 10.1038/s41467-023-41115-x
CrossrefPubMedSuche in Google Scholar
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Key words

protecting groups - racemization - sulfenyl group - solid-phase peptide synthesis

Significance

In peptide synthesis, epimerization is a long-standing problem, which is why various researchers have conducted investigations to suppress it. The authors have developed a thiol-labile amino protecting group that effectively suppress the epimerization.


Comment

DNPBS-protected amino acids were easily prepared in good yields for all proteinogenic amino acids. In the peptide coupling reaction, the use of DNPBS-protected amino acids suppressed epimerization more effectively than the use of carbamate-protected amino acids. This method was also applied to solid-phase peptide synthesis.




Publikationsverlauf

Artikel online veröffentlicht:
15. November 2023

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