STEREOSPECIFIC SYNTHESIS OF (2S,4R)-[5,5,5-H-2(3)]-LEUCINE

被引:44
作者
AUGUST, RA [1 ]
KHAN, JA [1 ]
MOODY, CM [1 ]
YOUNG, DW [1 ]
机构
[1] UNIV SUSSEX,SCH CHEM & MOLEC SCI,BRIGHTON BN1 9QJ,E SUSSEX,ENGLAND
关键词
LEUCINE; STEREOSPECIFIC SYNTHESIS; AMINO ACID; ISOTOPIC LABELING; BIOORGANIC;
D O I
10.1016/S0040-4039(00)61328-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first fully stereospecific synthesis of a sample of the amino acid (2S)-leucine labelled in only one of the diastereotopic methyl groups has been achieved using (2S)-pyroglutamic acid as a chiral template.
引用
收藏
页码:4617 / 4620
页数:4
相关论文
共 14 条
  • [1] SYNTHESIS OF (2S,4S)-[5-C-13] LEUCINE, (2R,4S)-[5-C-13] LEUCINE, AND (2RS)-[1,2-13C-2] LEUCINE
    ABERHART, DJ
    WEILLER, BH
    [J]. JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 1983, 20 (05) : 663 - 668
  • [2] ON THE ROLE OF LEUCINE IN TERPENOID METABOLISM
    ANASTASIS, P
    FREER, I
    OVERTON, KH
    PICKEN, D
    RYCROFT, DS
    SINGH, SB
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (11): : 2427 - 2436
  • [3] ACID AMIDE-REACTIONS L - ORTHO-AMIDES .I. SYNTHESIS AND PROPERTIES OF AMIDE ACETALES AND AMINALESTERS
    BREDERECK, H
    SIMCHEN, G
    REBSDAT, S
    KANTLEHNER, W
    HORN, P
    WAHL, R
    HOFFMANN, H
    GRIESHABER, P
    [J]. CHEMISCHE BERICHTE-RECUEIL, 1968, 101 (01): : 41 - +
  • [4] PATTERN OF INCORPORATION OF LEUCINE SAMPLES ASYMMETRICALLY LABELED WITH C-13 IN ISOPROPYL UNIT INTO C5-ISOPRENOID UNITS OF ECHINULINE AND FLAVOGLAUCINE
    CARDILLO, R
    FUGANTI, C
    GHIRINGHELLI, D
    GRASSELLI, P
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1977, (13) : 474 - 476
  • [5] SIMPLE SYNTHESIS OF L-GAMMA-CARBOXYGLUTAMATE AND DERIVATIVES THEREOF
    DANISHEFSKY, S
    BERMAN, E
    CLIZBE, LA
    HIRAMA, M
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (15) : 4385 - 4386
  • [6] FUGANTI C, 1979, TETRAHEDRON LETT, P2453
  • [7] SOME NEW NMR METHODS FOR TRACING THE FATE OF HYDROGEN IN BIOSYNTHESIS
    GARSON, MJ
    STAUNTON, J
    [J]. CHEMICAL SOCIETY REVIEWS, 1979, 8 (04) : 539 - 561
  • [8] GIBIAN H, 1961, LIEBIGS ANN CHEM, V640, P145
  • [9] KHAN JA, UNPUB
  • [10] H-1 AND C-13 NMR CHEMICAL-SHIFTS OF THE DIASTEREOTOPIC METHYL-GROUPS OF VALYL AND LEUCYL RESIDUES IN PEPTIDES AND PROTEINS
    NERI, D
    OTTING, G
    WUTHRICH, K
    [J]. TETRAHEDRON, 1990, 46 (09) : 3287 - 3296