A racemization test in peptide synthesis using 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMT-MM).
Racemization of the C-terminal amino acid (Ala) has been studied in various solvents during coupling between 4-methoxybenzyloxycarbonyl (Z(OMe))-Gly-L-Ala-OH and phenylalanine benzyl ester (H-Phe-OBzl) with 4-(4,6-dimethoxy-1,3,5-thiazin-2-yl)-4-methylmorpholinium chloride (DMT-MM). The reaction occurred without substantial racemization in AcOEt, tetrahydrofuran (THF), N,N-dimethylformamide (DMF), CH3CN, and 2-PrOH, while a slight racemization was observed in dimethyl sulfoxide (DMSO), EtOH, and MeOH. The extent of racemization may correlate with the polarity of the solvents.
Kunishima
Munetaka
M
Faculty of Pharmaceutical Sciences and High Technology Research Center, Kobe Gakuin University, Japan. kunisima@kgu-p.pharm.kobegakuin.ac.jp
Kitao
Akiko
A
Kawachi
Chiho
C
Watanabe
Yasunobu
Y
Iguchi
Shin
S
Hioki
Kazuhito
K
Tani
Shohei
S
D002851:Chromatography, High Pressure Liquid; D009025:Morpholines / Q000737:chemistry*; D009842:Oligopeptides / Q000138:chemical synthesis*; D012997:Solvents / Q000737:chemistry; D013237:Stereoisomerism
C467606:4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride; D009025:Morpholines; D009842:Oligopeptides; D012997:Solvents