外消旋化
肽合成
硫醇
氨基酸
化学
保护组
肽
吡啶
组合化学
群(周期表)
固相合成
立体化学
药物化学
有机化学
烷基
生物化学
作者
Yifei Zhou,Hongjun Li,Yi Huang,Jiahui Li,Gang Deng,Gong Chen,Zhen Xi,Chuanzheng Zhou
标识
DOI:10.1038/s41467-023-41115-x
摘要
In conventional solid-phase peptide synthesis (SPPS), α-amino groups are protected with alkoxycarbonyl groups (e.g., 9-fluorenylmethoxycarbonyl [Fmoc]). However, during SPPS, inherent side reactions of the protected amino acids (e.g., α-C racemization and aspartimide formation) generate by-products that are hard to remove. Herein, we report a thiol-labile amino protecting group for SPPS, the 2,4-dinitro-6-phenyl-benzene sulfenyl (DNPBS) group, which is attached to the α-amino group via a S-N bond and can be quantitatively removed in minutes under nearly neutral conditions (1 M p-toluenethiol/pyridine). The use of DNPBS greatly suppresses the main side reactions observed during conventional SPPS. Although DNPBS SPPS is not as efficient as Fmoc SPPS, especially for synthesis of long peptides, DNPBS and Fmoc are orthogonal protecting groups; and thus DNPBS SPPS and Fmoc SPPS can be combined to synthesize peptides that are otherwise difficult to obtain.
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