Synthesis and antibacterial activity of some new non-proteinogenic amino acids containing thiazole residues

被引：7
作者：
Stanchev, M [1 ]
Pajpanova, T [1 ]
Golovinsky, E [1 ]
机构：
[1] Bulgarian Acad Sci, Inst Mol Biol, BU-1113 Sofia, Bulgaria
来源：
AMINO ACIDS | 2000年 / 18卷 / 02期
关键词：
heterocyclic amino acids; peptide mimetics; thiazole; antimicrobial activity; canavanine; S-cysteine and homo-S-cysteinesulfonamides; alkaline protease;
D O I：
10.1007/s007260050015
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
Some new thioamides and thiazoles have been synthesized using canavanine, S-cysteine, homo-S-cysteinesulfonamides and their N-omega- aminoethylated derivatives as adducts in order to investigate the structure-antimicrobial activity relationships. The compounds showed substantial antibacterial activity in vitro against various gram-positive (Staphylococcus aureus, Bacillus cereus etc.) and gram-negative (Escherichia coli, Proteus vulgaris etc.) bacteria. These findings indicate that the presence of the thiazole residue is an essential factor for the antibacterial effect.
引用
收藏
页码：177 / 191
页数：15
相关论文
共 21 条
  • [1] THE USE OF ALKALINE PROTEASE FROM BACILLUS-SUBTILIS, STRAIN DY, FOR THE HYDROLYSIS OF AMINO-ACID AND PEPTIDE ESTERS
    ALEKSIEV, B
    SCHAMLIAN, P
    WIDENOV, G
    STOEV, S
    ZACHARIEV, S
    GOLOVINSKY, E
    [J]. HOPPE-SEYLERS ZEITSCHRIFT FUR PHYSIOLOGISCHE CHEMIE, 1981, 362 (10): : 1323 - 1329
  • [2] DOLASTATIN-10, A POWERFUL CYTOSTATIC PEPTIDE DERIVED FROM A MARINE ANIMAL - INHIBITION OF TUBULIN POLYMERIZATION MEDIATED THROUGH THE VINCA ALKALOID BINDING DOMAIN
    BAI, R
    PETTIT, GR
    HAMEL, E
    [J]. BIOCHEMICAL PHARMACOLOGY, 1990, 39 (12) : 1941 - 1949
  • [3] THE CHIRAL SYNTHESIS OF THIAZOLE AMINO-ACID ENANTIOMERS
    BREDENKAMP, MW
    HOLZAPFEL, CW
    VANZYL, WJ
    [J]. SYNTHETIC COMMUNICATIONS, 1990, 20 (15) : 2235 - 2249
  • [4] ELNAGGAR AM, 1982, INT J PEPT PROT RES, V19, P408
  • [5] HUDSON D, 1988, 900001 MILL GEN BIOS
  • [6] IRELAND CM, 1989, BIOORGANIC MARINE CH, P1001
  • [7] KERAMAMIDE F, A NEW THIAZOLE-CONTAINING PEPTIDE FROM THE OKINAWAN MARINE SPONGE THEONELLA SP
    ITAGAKI, F
    SHIGEMORI, H
    ISHIBASHI, M
    NAKAMURA, T
    SASAKI, T
    KOBAYASHI, J
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (20) : 5540 - 5542
  • [8] MIERSCH I, 1997, GUANIDINO COMPOUNDS, V2, P401
  • [9] SYNTHETIC STUDIES TOWARDS CYCLIC-PEPTIDES - CONCISE SYNTHESIS OF THIAZOLINE AND THIAZOLE CONTAINING AMINO-ACIDS
    NORTH, M
    PATTENDEN, G
    [J]. TETRAHEDRON, 1990, 46 (24) : 8267 - 8290
  • [10] NORTHCOTE PT, 1991, TETRAHEDRON, V44, P6411
123