Journal of the Chemical Society. Perkin transactions I p. 3545 - 3548 (1994)
Update date:2022-08-04
Topics:
Easton, Christopher J.
Hutton, Craig, A.
The four stereoisomers of <3-2H1>phenylalanine have been prepared, each as a single enantiomer in ca. 98percent diastereoisomeric excess and with ca. 99percent deuterium incorporation, by side-chain bromination of phenylalanine derivatives, followed by deuteriolysis of each of the diastereoisomeric product bromides with deuterium over 5percent palladium-on-carbon.The latter reactions proceeded with retention of configuration. (2R,3S)-<3-2H1>Phenylalanine reacted with (S)-phenylalanine ammonia-lyase to give <3-2H1>-trans-cinnamic acid, with 92percent deuterium incorporation, while the (2R,3R)-stereoisomer of the deuterated phenylalanine gave <3-2H1>-trans-cinnamic acid with 27percent deuterium incorporation.These results indicate that reaction of (R)-phenylalanine with the enzyme involves mainly loss of the 3-pro-R hydrogen and ammonia, in an antiperiplanar elimination process analogous to that previously reported for (S)-phenylalanine, while a minor pathway for reaction of (R)-phenylalanine is either isomerization to (S)-phenylalanine, before elimination, or synperiplanar elimination.
View MoreMTT Pharma & Bio-technology Co.,Ltd(expird)
Contact:+86-21-58407925
Address:Room2019, Building C, Tomson Center, No.158, Zhang Yang Road, Shanghai, China
SHANGHAI ARCADIA BIOTECHNOLOGY LTD.
Contact:+86-21-61353236
Address:SUITE 901, BUILDING WENSLI, 1378 LU JIA BANG RD, SHANGAHI 200011, P.R.CHINA
Ceresking Ecology & Technology co.,ltd
Contact:86 22 66218397
Address:Room 1613, Zheshang Mansion, No. 1988, Yingbin Avenue, Binhai New District, Tianjin,China.
Hubei Xiangxi Chemical Industry Co.,Ltd
Contact:+86-710-3454830
Address:No.7, Daqing East Road, Xiangfan City, Hubei Province, China
Contact:86-512-69362780,69362785
Address:No.69 Weixin Road,Weiting Town,Suzhou Industrial Park
Doi:10.1016/S0957-4166(03)00286-6
(2003)Doi:10.1002/ejoc.202100500
(2021)Doi:10.1021/ja002457e
(2001)Doi:10.1021/ja0023377
(2001)Doi:10.1016/S0040-4020(01)90759-8
(1971)Doi:10.1021/ja002723o
(2001)
