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 MoreTai zhou world Pharm & Chem Co., Ltd
Contact:+86-576-85301198
Address:Rome 1001,wangjiang plaza,unti 2,jinshan east Road linhai,zhejiang,china
website:http://www.chinabarton.com
Contact:+86-573-82719618
Address:No. 162 Fumin Road, Honghe Town,
Penglai Qianwei Chemical Co., Ltd.
Contact:86-535-3357802
Address:Shahelu (north), Penglai, Shandong, China
Jiangxi Dongbang Pharmaceutical Co., Ltd.
Contact:+86-795-4433603, 4433388
Address:Fengxin Industrial Park, Fengxin County, Jiangxi Province, P.R.C
Shouguang Nuomeng Chemical Co., Ltd.
Contact:+86-536-5119508/18363669993
Address:Hou Zhen Industrial Park, Shouguang, Shandong, China
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)
