Synthesis 2013; 45(20): 2843-2852
DOI: 10.1055/s-0033-1339550
paper
© Georg Thieme Verlag Stuttgart · New York

A Convenient and Efficient Synthesis of Dipeptidyl Benzoxaboroles and Their Peptidomimetics

Zhengyan Fu*
State Key Laboratory of Biotherapy, West China Hospital, Sichuan University, Chengdu 610041, P. R. of China   Fax: +86(28)85503817   eMail: zhengyanfu@scu.edu.cn   eMail: xieym@scu.edu.cn
,
Jiangpeng He
State Key Laboratory of Biotherapy, West China Hospital, Sichuan University, Chengdu 610041, P. R. of China   Fax: +86(28)85503817   eMail: zhengyanfu@scu.edu.cn   eMail: xieym@scu.edu.cn
,
Aiping Tong
State Key Laboratory of Biotherapy, West China Hospital, Sichuan University, Chengdu 610041, P. R. of China   Fax: +86(28)85503817   eMail: zhengyanfu@scu.edu.cn   eMail: xieym@scu.edu.cn
,
Yongmei Xie*
State Key Laboratory of Biotherapy, West China Hospital, Sichuan University, Chengdu 610041, P. R. of China   Fax: +86(28)85503817   eMail: zhengyanfu@scu.edu.cn   eMail: xieym@scu.edu.cn
,
Yuquan Wei
State Key Laboratory of Biotherapy, West China Hospital, Sichuan University, Chengdu 610041, P. R. of China   Fax: +86(28)85503817   eMail: zhengyanfu@scu.edu.cn   eMail: xieym@scu.edu.cn
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Publikationsverlauf

Received: 22. Mai 2013

Accepted after revision: 17. Juli 2013

Publikationsdatum:
06. August 2013 (online)


Abstract

We have developed a convenient and efficient method for the synthesis of dipeptidyl benzoxaboroles and their peptidomimetics. The novel dipeptidyl benzoxaboroles were obtained by the protecting-group-free coupling of 6-amino-1,3-dihydro-2,1-benz­oxaborol-1-ol with various N-(arylcarbonyl)phenylalanines. Bioisosteric replacement of the terminal amide moiety of dipeptidyl benzoxaboroles by 1,3,4-oxadiazoles or 4H-3,1-benzothiazin-4-one provided their peptidomimetics with good molecular diversity. These transformations were based on the pluripotency of methyl (S)-2-isothiocyanato-3-phenylpropanoate and were highlighted by mild reaction conditions, high atom efficiency, and good to excellent isolated yields. This method is a valuable addition to the development of novel drug-like boronic acid molecules.

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