Synthesis and assignment of stereochemistry of the antibacterial cyclic peptide xenematide

被引:19
|
作者
Hung, Kuo-yuan [1 ]
Harris, Paul W. R. [1 ]
Heapy, Amanda M. [1 ]
Brimble, Margaret A. [1 ]
机构
[1] Univ Auckland, Dept Chem, Auckland, New Zealand
关键词
RESISTANCE;
D O I
10.1039/c0ob00315h
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of the antimicrobial cyclic peptide xenematide was accomplished by Fmoc solid phase peptide synthesis and the key esterification reaction was achieved using a modified Yamaguchi esterification. Comparison of the optical rotation and NMR data of the synthesized diastereomers to that of the natural product confirmed the structure of xenematide to be PA-L-[Thr-L-Trp-D-Trp-beta-Ala]. (PA = phenylacetyl).
引用
收藏
页码:236 / 242
页数:7
相关论文
共 50 条
  • [31] Synthesis and antibacterial activity of peptide deformylase inhibitors
    Huntington, KM
    Yi, T
    Wei, YM
    Pei, DH
    BIOCHEMISTRY, 2000, 39 (15) : 4543 - 4551
  • [32] Synthesis and Antibacterial Application of Antimicrobial Peptide CLKGPIC
    Wu, Han
    Cong, Hai-Lin
    Shen, You-Qing
    Niu, Qing-Hai
    Yu, Bing
    INTEGRATED FERROELECTRICS, 2024, 240 (02) : 271 - 277
  • [33] SYNTHESIS AND ASSIGNMENT OF STRUCTURE TO A SATURATED CYCLIC ACYL IMIDATE
    BHATIA, PL
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1979, 17 (03): : 293 - 294
  • [34] The synthesis of the cyclic antibacterial peptide Kawaguchipeptin B on 11 different DVB cross-linked PS resins
    Rana, S
    Dubuc, J
    Bradley, M
    White, P
    TETRAHEDRON LETTERS, 2000, 41 (26) : 5135 - 5139
  • [35] TOTAL SYNTHESIS OF THE POLLEN-GROWTH INHIBITOR (-)-EMENIVEOL - ASSIGNMENT OF ABSOLUTE STEREOCHEMISTRY
    SHIMOKAWA, K
    SMITH, AB
    TETRAHEDRON LETTERS, 1993, 34 (46) : 7383 - 7384
  • [36] Antibacterial agents based on the cyclic D,L-α-peptide architecture
    Fernandez-Lopez, S
    Kim, HS
    Choi, EC
    Delgado, M
    Granja, JR
    Khasanov, A
    Kraehenbuehl, K
    Long, G
    Weinberger, DA
    Wilcoxen, KM
    Ghadiri, MR
    NATURE, 2001, 412 (6845) : 452 - 455
  • [37] Total Synthesis and Assignment of Stereochemistry of Raocyclamide Cyclopeptides from Cyanobacterium Oscillatoria raoi
    Freeman, D. J.
    Pattenden, G.
    Tetrahedron Letters, 39 (20):
  • [38] Antibacterial agents based on the cyclic d,l-α-peptide architecture
    Sara Fernandez-Lopez
    Hui-Sun Kim
    Ellen C. Choi
    Mercedes Delgado
    Juan R. Granja
    Alisher Khasanov
    Karin Kraehenbuehl
    Georgina Long
    Dana A. Weinberger
    Keith M. Wilcoxen
    M. Reza Ghadiri
    Nature, 2001, 412 : 452 - 455
  • [39] Total synthesis and assignment of stereochemistry of raocyclamide cyclopeptides from cyanobacterium Oscillatoria raoi
    Freeman, DJ
    Pattenden, G
    TETRAHEDRON LETTERS, 1998, 39 (20) : 3251 - 3254
  • [40] Synthesis, antibacterial and anticonvulsant evaluations of some cyclic enaminones
    Edafiogho, Ivan O.
    Phillips, Oludotun A.
    Udo, Edet E.
    Samuel, Santosh
    Rethish, Beigy
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2009, 44 (03) : 967 - 975