A racemization test in peptide synthesis using 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMT-MM)

被引：29

作者：

Kunishima, M ^{[1
]}

Kitao, A

Kawachi, C

Watanabe, Y

Iguchi, S

Hioki, K

Tani, S

机构：

[1] Kobe Gakuin Univ, Fac Pharmaceut Sci, Nishi Ku, Kobe, Hyogo 6512180, Japan

[2] Kobe Gakuin Univ, High Technol Res Ctr, Nishi Ku, Kobe, Hyogo 6512180, Japan

来源：

CHEMICAL & PHARMACEUTICAL BULLETIN | 2002年 / 50卷 / 04期

关键词：

dehydrating condensation; racemization; peptide; amide;

D O I：

10.1248/cpb.50.549

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

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.

引用

页码：549 / 550

页数：2

共 10 条

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[2]

KAMINSKI ZJ, 1987, SYNTHESIS-STUTTGART, P917

[3]

Kemp D. S., 1979, PEPTIDES ANAL SYNTHE, V1, P315

[4]

KISO Y, 1980, PEPTIDE CHEM, P71