Total Synthesis of Unguisin A

被引：27
作者：
Hunter, Luke [1 ]
Chung, Jonathan H. [1 ]
机构：
[1] Univ Sydney, Sch Chem, Sydney, NSW 2006, Australia
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 76卷 / 13期
关键词：
CYCLIC PEPTIDE; CYCLIZATION; PRODUCTS;
D O I：
10.1021/jo200813a
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The first synthesis of the gamma-aminobutyric acid (GABA)-containing cyclic heptapeptide unguisin A is reported, confirming the structure of this natural product. Macrocyclization of a flexible GABA-containing linear precursor is found to proceed rapidly and in good yield.
引用
收藏
页码：5502 / 5505
页数：4
相关论文
共 27 条
  • [1] Thiopeptide Antibiotic Biosynthesis
    Arndt, Hans-Dieter
    Schoof, Sebastian
    Lu, Jin-Yong
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (37) : 6770 - 6773
  • [2] Bewley CA, 1998, ANGEW CHEM INT EDIT, V37, P2163, DOI 10.1002/(SICI)1521-3773(19980904)37:16<2162::AID-ANIE2162>3.0.CO
  • [3] 2-2
  • [4] Chan W., 1999, Fmoc solid phase peptide synthesis: a practical approach
  • [5] Chen SL, 1998, ANTI-CANCER DRUG DES, V13, P501
  • [6] Bioactive pseudopeptidic analogues and cyclostereoisomers of osteogenic growth peptide C-terminal pentapeptide, OGP(10-14)
    Chen, YC
    Muhlrad, A
    Shteyer, A
    Vidson, M
    Bab, I
    Chorev, M
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2002, 45 (08) : 1624 - 1632
  • [7] The cyclization of peptides and depsipeptides
    Davies, JS
    [J]. JOURNAL OF PEPTIDE SCIENCE, 2003, 9 (08) : 471 - 501
  • [8] Cyclization of all-L-pentapeptides by means of 1-hydroxy-7-azabenzotriazole-derived uronium and phosphonium reagents
    Ehrlich, A
    Heyne, HU
    Winter, R
    Beyermann, M
    Haber, H
    Carpino, LA
    Bienert, M
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (25) : 8831 - 8838
  • [9] FAIRLIE DP, 1995, CURR MED CHEM, V2, P654
  • [10] Recent progress of the synthetic studies of biologically active marine cyclic peptides and depsipeptides
    Hamada, Y
    Shioiri, T
    [J]. CHEMICAL REVIEWS, 2005, 105 (12) : 4441 - 4482
123