METHODS FOR THE SYNTHESIS OF L-LEUCINE SELECTIVELY LABELED WITH C-13 OR DEUTERIUM IN EITHER DIASTEREOTOPIC METHYL-GROUP

被引:18
作者
KELLY, NM
REID, RG
WILLIS, CL
WINTON, PL
机构
[1] UNIV BRISTOL, SCH CHEM, BRISTOL BS8 1TS, AVON, ENGLAND
[2] AMERSHAM INT PLC, CARDIFF CF4 7YT, S GLAM, WALES
关键词
D O I
10.1016/0040-4039(95)01738-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A versatile approach is described for the enantioselective synthesis of isotopically labelled L-leucine involving the preparation of 2-oxo-4-methylpentanoic acid labelled selectively with carbon-13 or deuterium in either the pro-R or pro-S methyl group followed by a reductive amination of the ketone catalysed by leucine dehydrogenase. This strategy is applied to the total synthesis of (2S,4R)-[5,5,5-D-3]-leucine using CD3I as the source of deuterium.
引用
收藏
页码:8315 / 8318
页数:4
相关论文
共 9 条
  • [1] August R.A., Khan J.A., Moody C.M., Young D.W., Tetrahedron Lett., 33, (1992)
  • [2] Hill R.K., Abacherli C., Hagishita S., Can. J. Chem., 72, (1994)
  • [3] Cardillo R., Fuganti C., Ghiringhelli D., Grasselli P., J. Chem. Soc, Chem. Commun., (1977)
  • [4] Sylvester S.R., Yan S.Y., Stevens C.M., Biochemistry, 20, (1981)
  • [5] Kelly N.M., O'Neill B.C., Proben J., Reid G., Stephen R., Wang T., Willis C.L., Winton P., Tetrahedron Lett., 35, (1994)
  • [6] Kovacs L., Recuil de Trav. Chim. de Pays-Bas, 112, (1993)
  • [7] Cooper A.J.L., Ginos J.Z., Meister A., Chem. Rev., 83, (1983)
  • [8] Evans D.A., Bartroli J., Shih T.L., J. Am. Chem. Soc, 103, (1981)
  • [9] Evans D.A., Ennis M.D., Mathre D.J., J. Am. Chem. Soc, 104, (1982)