Journal of Organic Chemistry p. 1789 - 1795 (1994)
Update date:2022-07-30
Topics:
Kazmierski, Wieslaw M.
Urbanczyk-Lipkowska, Zofia
Hruby, Victor J.
The synthesis of all four diastereomers of α,β-dimethylphenylalanine (4) as well as those of α,β-dimethyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (5 and 6) have been accomplished in high yield and high optical purity.Molecular mechanics calculations on the Nα-acetyl and N-methylcarboxamide derivatives of (3R,4R)-6 and (3R,4S)-5 indicate large and moderate energy stabilization for the gauche(-) but not the gauche(+) side-chain conformers of (3R,4S)-5 and (3R,4R)-6, respectively.By symmetry rules, the same holds for (3S,4R)-5 and (3S,4S)-6, respectively.Thus, these amino acids are potential building blocks for the topographical design of peptides (Kazmierski et al., J.Am.Chem.Soc. 1991, 113, 2275-2283) by providing acylated 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid derivatives in which a gauche(-) and not a gauche(+) side-chain conformation is energetically more stable for the L amino acid.Synthetic details and implications of these new amino acids for peptide and protein design are discussed.
View MoreContact:+86-158-5814-5714
Address:No.9 YanAn Road,Hangzhou,Zhejiang,China
Ceresking Ecology & Technology co.,ltd
Contact:86 22 66218397
Address:Room 1613, Zheshang Mansion, No. 1988, Yingbin Avenue, Binhai New District, Tianjin,China.
Chengdu Gelipu Biotechnology Co., Ltd.
website:http://www.glp-china.com
Contact:86-28-82610909
Address:chegndu
ningbo easun bio-tech co., ltd
website:http://www.easunbiotech.com
Contact:+8657462089878
Address:Ru Lake Road No. 23, Simen Town , Yuyao City,Zhejiang province
Daicel Chiral Technologies (China)CO.,LTD
Contact:021-5046-0086*8
Address:Part C, FL 5, the 16th Building, No. 69, XiYa Road, WaiGaoQiao Free Trade Zone, Shanghai, 200131, P.R.China
Doi:10.1002/anie.201206918
(2012)Doi:10.1039/c3nj00032j
(2013)Doi:10.3390/molecules18021464
(2013)Doi:10.1016/j.tet.2012.08.042
(2012)Doi:10.1021/acsmedchemlett.7b00170
(2017)Doi:10.1021/jo502929x
(2015)