Citation: Zuo Chao, Zhang Baochang, Wu Meng, Bierer Donald, Shi Jing, Fang Ge-Min. Chemical synthesis and racemic crystallization of rat C5a-desArg[J]. Chinese Chemical Letters, ;2020, 31(3): 693-696. doi: 10.1016/j.cclet.2019.08.039 shu

Chemical synthesis and racemic crystallization of rat C5a-desArg

Zuo Chao ^a,b ,
Zhang Baochang ^b ,
Wu Meng ^a ,
Bierer Donald ^d ,
Shi Jing ^c,*, ,
Fang Ge-Min ^a,*,

a.
School of Life Science, Institutes of Physical Science and Information Technology, Anhui University, Hefei 230601, China
b.
Department of Chemistry, Tsinghua University, Beijing 100084, China
c.
Department of Chemistry, University of Science and Technology of China, Hefei 230601, China
d.
Bayer AG, Department of Medicinal Chemistry, Aprather Weg 18 A, 42096, Wuppertal, Germany

shijing@ustc.edu.cn

fanggm@ahu.edu.cn

Received Date: 24 June 2019
Revised Date: 5 August 2019
Accepted Date: 23 August 2019
Available Online: 26 August 2019

Figures(4)

The deletion of the C-terminal arginine of the anaphylatoxin protein C5a reduces it receptor binding affinity. Understanding how C-terminal arginine affects the structure and bioactivity of C5a is important for the development of C5a C-terminal mimics as drug candidates. Herein, we report the total chemical synthesis of rat C5a and its D-enantiomer with its C-terminal arginine deleted, namely L-rC5a-desArg and D-rC5a-desArg. The structure of rC5a-desArg was then determined by racemic crystallography for the first time. The C-terminal residues of rC5a-Arg were found to expand from the fourth helix in a continuous helical conformation. This C-terminal conformation is significantly different from that of the previously reported full-length of C5a, indicating that the deletion of C-terminal arginine residue could result in the destruction of a positively charged surface formed by two adjacent Arg residues in C5a.
- Anaphylatoxin C5a,
- Racemic crystallization,
- Solid phase peptide synthesis,
- Chemical protein synthesis,
- Hydrazide-based native chemical ligation
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