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
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.
