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 MoreWuhan Silworld Chemical Co.,Ltd
website:http://www.silworldchemical.com
Contact:+86-27-85613400
Address:No.198 jiangjun Road, Wuhan,China 430033
JiangXi Hong Run Chemical Co., Ltd
Contact:+86-0791-88521351
Address:XingHuo industrial zone in YongXiu county
Shanghai Pengkai Chemical Co.,Ltd
Contact:+86-21-60526671
Address:No.4226 Duzhuang Rd Minhang District Shanghai China
Hebei Lead Bio-Chemicals Co., Ltd.
website:http://www.ldbiochem.com
Contact:+86-311-87826503
Address:481, Heping West Road, Shijiazhuang,China
Anhui Xinyuan Technology Co.,Ltd
Contact:0086-559-3515800
Address:No.16 Zijin Rd, Circular Economic Zone, Huizhou District, Huangshan Anhui 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)