Synthesis and NMR characteristics of N-acetyl-4-nitro, N-acetyl-5-nitro, N-acetyl-6-nitro and N-acetyl-7-nitrotryptophan methyl esters

被引：6
|
作者：
King, Russell R. [1 ]
Calhoun, Larry A. [2 ]
机构：
[1] Agr & Agr Food Canada, Potato Res Ctr, Fredericton, NB E3B 4Z7, Canada
[2] Univ New Brunswick, Dept Chem, Fredericton, NB E3B 5A3, Canada
来源：
MAGNETIC RESONANCE IN CHEMISTRY | 2009年 / 47卷 / 03期
关键词：
NMR; (1)H NMR; (13)C NMR; nitroindoles; nitrotryptophans; TWO-DIMENSIONAL NMR; STREPTOMYCES-SCABIES; PHYTOTOXINS; TRYPTOPHAN; THAXTOMIN; PROTEINS;
D O I：
10.1002/mrc.2377
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
N-acetyl-4-nitrotryptophan methyl ester (2), N-acetyl-5-nitrotryptophan methyl ester (3), N-acetyl-6-nitrotryptophan methyl ester (4) and N-acetyl-7-nitrotryptophan methyl ester (5) were synthesized through a modified malonic ester reaction of the appropriate nitrogramine analogs followed by methylation with BF(3)-methanol. Assignments of the (1)H and (13)C NMR chemical shifts were made using a combination of (1)H-(1)H COSY, (1)H-(13)C HETCOR and (1)H-(13)C selective INEPT experiments. Copyright (C) 2008 Crown in the right of Canada. Published by John Wiley & Sons, Ltd
引用
收藏
页码：273 / 276
页数：4
相关论文
共 50 条
  • [31] CONFORMATIONAL CHARACTERISTICS OF THE N-ACETYL-N'-METHYLAMIDES OF THE 4 (LYS, TYR) DIPEPTIDES
    RAE, ID
    LEACH, SJ
    MINASIAN, E
    SMITH, JA
    ZIMMERMAN, SS
    WEIGOLD, JA
    HODES, ZI
    NEMETHY, G
    WOODY, RW
    SCHERAGA, HA
    INTERNATIONAL JOURNAL OF PEPTIDE AND PROTEIN RESEARCH, 1981, 17 (05): : 575 - 592
  • [32] An alternative synthesis of N-acetyl-4-deoxyneuraminic acid
    Ooi, HC
    Marcuccio, SM
    Jackson, WR
    AUSTRALIAN JOURNAL OF CHEMISTRY, 1999, 52 (10) : 937 - 940
  • [33] SYNTHETIC STUDIES ON SIALOGLYCOCONJUGATES .17. SYNTHESIS OF 4-O-ACETYL-N-ACETYLNEURAMINIC, 9-O-ACETYL-N-ACETYLNEURAMINIC, AND 4,9-DI-O-ACETYL-N-ACETYLNEURAMINIC ACIDS AND THEIR DERIVATIVES
    HASEGAWA, A
    MURASE, T
    OGAWA, M
    ISHIDA, H
    KISO, M
    JOURNAL OF CARBOHYDRATE CHEMISTRY, 1990, 9 (04) : 415 - 428
  • [34] The effect of N-acetyl-cysteine and N-ω-nitro-L-arginine methyl ester treatment on lipopolysaccharide-induced oxidative stress in lung of rats
    Türkoglu, ÜM
    Öztezcan, S
    Tamer-Toptani, S
    Uysal, M
    Toker, GA
    BIOCHEMICAL ARCHIVES, 1998, 14 (02) : 139 - 146
  • [35] The synthesis of N-acetyl-β-L-fucosamine-1-phosphate and uridine 5′-diphospho-N-acetyl-β-L-fucosamine
    Illarionov, PA
    Torgov, VI
    Hancock, I
    Shibaev, VN
    RUSSIAN CHEMICAL BULLETIN, 2000, 49 (11) : 1891 - 1894
  • [36] An efficient synthesis of des-N-methyl-N-acetyl erythromycin derivatives via the N-oxide
    Ku, YY
    Riley, D
    Patel, H
    Yang, CX
    Liu, JH
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1997, 7 (09) : 1203 - 1206
  • [37] STEROIDS .3. THE EPIMERIC N-ACETYL-3-AMINOCHOLEST-4-ENES AND N-ACETYL-3-AMINOCHOLEST-4-5-ENES
    BANNARD, RAB
    MCKAY, AF
    CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1955, 33 (06): : 1166 - 1170
  • [38] Stereoselective synthesis of N-acetyl thiochitooligosaccharides. Different behaviours of methyl N-acetyl-alpha- and -beta-thiochitobiosides during acetolysis
    Wang, LX
    Lee, YC
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (06): : 581 - 591
  • [39] 4-N-acetylamino-5-[N-acetyl-N-(tetra-O-acetyl-β-D-glucopyranosyl)amino]-1,3-dimethyluracil
    Rodrigo, AS
    Montiel, MN
    Cobo, J
    Low, JN
    Glidewell, C
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2006, 62 : O969 - O971
  • [40] SYNTHESIS OF FLUORESCENT 7,8,9-TRI-O-ACETYL-N-ACETYLNEURAMINIC AND 4-O-ACETYL-N-ACETYLNEURAMINIC ACID ALPHA-THIOKETOSIDES
    ROTH, A
    FAILLARD, H
    LIEBIGS ANNALEN DER CHEMIE, 1993, (05): : 485 - 489
12345