IMPROVED SOLID-PHASE SYNTHESIS OF C-TERMINAL PEPTIDE ALDEHYDES

被引:80
作者
FEHRENTZ, JA
PARIS, M
HEITZ, A
VELEK, J
LIU, CF
WINTERNITZ, F
MARTINEZ, J
机构
[1] FAC PHARM MONTPELLIER,CNRS,CHIM & PHARMACOL MOLECULES INTERET BIOL LAB,F-34060 MONTPELLIER,FRANCE
[2] FAC PHARM MONTPELLIER,CNRS,UNITE MIXTE,F-34060 MONTPELLIER,FRANCE
关键词
D O I
10.1016/0040-4039(95)01646-Y
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new linker based on the Weinreb amide was developed in order to synthesize from peptidyl-resin the corresponding aldehydic peptides by reduction with LiAlH4. This new reaction was tested with N-protected amino-residues and with tripeptides to obtain the corresponding aldehydes without racemisation.
引用
收藏
页码:7871 / 7874
页数:4
相关论文
共 19 条
  • [1] LEUPEPTINS NEW PROTEASE INHIBITORS FROM ACTINOMYCETES
    AOYAGI, T
    TAKEUCHI, T
    MATSUZAKI, A
    KAWAMURA, K
    KONDO, S
    HAMADA, M
    MAEDA, K
    UMEZAWA, H
    [J]. JOURNAL OF ANTIBIOTICS, 1969, 22 (06) : 283 - +
  • [2] HIGHLY-ACTIVE AND SELECTIVE ANTICOAGULANTS - D-PHE-PRO-ARG-H, A FREE TRIPEPTIDE ALDEHYDE PRONE TO SPONTANEOUS INACTIVATION, AND ITS STABLE N-METHYL DERIVATIVE, D-MEPHE-PRO-ARG-H
    BAJUSZ, S
    SZELL, E
    BAGDY, D
    BARABAS, E
    HORVATH, G
    DIOSZEGI, M
    FITTLER, Z
    SZABO, G
    JUHASZ, A
    TOMORI, E
    SZILAGYI, G
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (06) : 1729 - 1735
  • [3] BASAK A, 1994, INT J PEPT PROT RES, V44, P253
  • [4] SYNTHESIS OF A POTENT, REVERSIBLE INHIBITOR OF INTERLEUKIN-1-BETA CONVERTING ENZYME
    CHAPMAN, KT
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1992, 2 (06) : 613 - 618
  • [5] FEHRENTZ JA, 1983, SYNTHESIS-STUTTGART, P676
  • [6] ALDEHYDIC PEPTIDES INHIBITING RENIN
    FEHRENTZ, JA
    HEITZ, A
    CASTRO, B
    CAZAUBON, C
    NISATO, D
    [J]. FEBS LETTERS, 1984, 167 (02) : 273 - 276
  • [7] FEHRENTZ JA, 1985, INT J PEPT PROT RES, V26, P236
  • [8] GRAYBILL TL, 1994, INT J PEPT PROT RES, V44, P173
  • [9] AN EFFECTIVE SYNTHESIS OF N-(9-FLUORENYLMETHYLOXYCARBONYL) ALPHA-AMINO ALDEHYDES FROM S-BENZYL THIOESTERS
    HO, PT
    NGU, KY
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (08) : 2313 - 2316
  • [10] ITO A, 1975, CHEM PHARM BULL, V23, P3081