Journal of Organic Chemistry p. 8155 - 8170 (1995)
Update date:2022-07-31
Topics:
Li, Wenhao
Hanau, Cathleen E.
d'Avignon, Andre
Moeller, Kevin D.
This manuscript describes a convenient procedure for the synthesis of peptide fragments containing 6,5-bicyclic lactam-based conformational constraints.The syntheses capitalize on an electrochemical oxidation to functionalize a substituted proline derivative, an N-acyliminium ion-initiated cyclization in order to form a transient seven-membered-ring lactam, and a rearragement reaction to form the desired six-membered-ring lactam.The bicyclic lactam products were converted into peptide building blocks and the stereochemistry of the building blocks assigned using two-dimensional NMR techniques.Once synthesized, the building blocks were readily incorporated into peptide fragments with the use of standard peptide synthesis techniques.The synthetic route employed was shown to be compatible with both aryl and branched amino acid side chains.
View MoreContact:86-574-83851061 86-574-87083208
Address:Room 905, No.3 Building,East Business Center, 456 Xingning Road, Ningbo City,China
Beijing Merson Pharmaceutical Co., Ltd
Contact:0086-10-80484934 0086-10-80484574/
Address:2nd Floor , No. 2 Building , No. 14 Houshayu Duan, Jingmi Road ,Shunyi District , Beijing 101318, P.R.China
NANCHANG QINZHI SCI&TEC.CO.,LTD
Contact:+86-13687004106
Address:Hero South Road,Hero Zone,Nanchang,Jiangxi,China
Anqing World Chemical Co., Ltd.
Contact:+86-556-5800026
Address:Daguan Economic Development Zone of circular economy industrial park Anqing City Anhui province
Contact:USA:563-513-3839
Address:No.121TANGU EAST STREET,SHIJIAZHAUNG,CHINA
Doi:10.1021/jm950568w
(1996)Doi:10.1039/dt9960000177
(1996)Doi:10.1021/om950750v
(1996)Doi:10.1021/jo026032h
(2002)Doi:10.1016/S0040-4039(01)93881-X
(1989)Doi:10.1021/bi00801a032
(1971)