Contemporary Approaches to α,β-Dehydroamino Acid Chemical Modifications

doi:10.1007/s40242-021-1307-z

高等学校化学研究 ›› 2021, Vol. 37 ›› Issue (5): 1044-1054.doi: 10.1007/s40242-021-1307-z

Contemporary Approaches to α,β-Dehydroamino Acid Chemical Modifications

ZHANG Mengqian¹, HE Peiyang¹, LI Yanmei^1,2,3

1. Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology, Department of Chemistry, Tsinghua University, Beijing 100084, P. R. China;
2. Beijing Institute for Brain Disorders, Beijing 100069, P. R. China;
3. Center for Synthetic and Systems Biology, Tsinghua University, Beijing 100084, P. R. China

收稿日期:2021-08-10 修回日期:2021-09-06 出版日期:2021-10-01 发布日期:2021-09-30
通讯作者: LI Yanmei E-mail:liym@mail.tsinghua.edu.cn
基金资助:
This work was supported by the National Key R&D Program of China (Nos.2018YFA0507600, 2019YFA0904200) and the National Natural Science Foundation of China(No.92053108).

Contemporary Approaches to α,β-Dehydroamino Acid Chemical Modifications

ZHANG Mengqian¹, HE Peiyang¹, LI Yanmei^1,2,3

1. Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology, Department of Chemistry, Tsinghua University, Beijing 100084, P. R. China;
2. Beijing Institute for Brain Disorders, Beijing 100069, P. R. China;
3. Center for Synthetic and Systems Biology, Tsinghua University, Beijing 100084, P. R. China

Received:2021-08-10 Revised:2021-09-06 Online:2021-10-01 Published:2021-09-30
Contact: LI Yanmei E-mail:liym@mail.tsinghua.edu.cn
Supported by:
This work was supported by the National Key R&D Program of China (Nos.2018YFA0507600, 2019YFA0904200) and the National Natural Science Foundation of China(No.92053108).

摘要/Abstract

摘要： As one of the most common unnatural amino acids(uAAs), α, β-dehydroamino acids(α,β-dhAAs) can be found in various ribosomally synthesized and post-translationally modified peptides(RiPPs) and other naturally occurring peptides. In recent years, novel reactions for α,β-dhAA modification continue to emerge. Due to their unique electrophilicity different from 20 natural amino acids, α,β-dhAAs, especially dehydroalanine(Dha), have become powerful tools for site-selective protein modification. In this review, we mainly focus on the latest research progress of C-C and C-heteroatom(C-X, X=S, N, Se, Si, P, B) bond formation methods based on α,β-dhAAs in the past five years. Particularly, we pay much attention to the α,β-dhAA derivatization methodologies used in the late-stage modification for natural peptides and proteins. In addition, we also focus on the downstream functionalization and therapeutic biologic applications of these modifications.

关键词: Dehydroamino acid, Peptide, Protein, Chemical modification

Abstract: As one of the most common unnatural amino acids(uAAs), α, β-dehydroamino acids(α,β-dhAAs) can be found in various ribosomally synthesized and post-translationally modified peptides(RiPPs) and other naturally occurring peptides. In recent years, novel reactions for α,β-dhAA modification continue to emerge. Due to their unique electrophilicity different from 20 natural amino acids, α,β-dhAAs, especially dehydroalanine(Dha), have become powerful tools for site-selective protein modification. In this review, we mainly focus on the latest research progress of C-C and C-heteroatom(C-X, X=S, N, Se, Si, P, B) bond formation methods based on α,β-dhAAs in the past five years. Particularly, we pay much attention to the α,β-dhAA derivatization methodologies used in the late-stage modification for natural peptides and proteins. In addition, we also focus on the downstream functionalization and therapeutic biologic applications of these modifications.

Key words: Dehydroamino acid, Peptide, Protein, Chemical modification

ZHANG Mengqian, HE Peiyang, LI Yanmei. Contemporary Approaches to α,β-Dehydroamino Acid Chemical Modifications[J]. 高等学校化学研究, 2021, 37(5): 1044-1054.

ZHANG Mengqian, HE Peiyang, LI Yanmei. Contemporary Approaches to α,β-Dehydroamino Acid Chemical Modifications[J]. Chemical Research in Chinese Universities, 2021, 37(5): 1044-1054.

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Contemporary Approaches to α,β-Dehydroamino Acid Chemical Modifications

Contemporary Approaches to α,β-Dehydroamino Acid Chemical Modifications

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