Synthesis and structure revision of symplocin A

被引:0
作者
Shao, Lu-Ping [1 ]
Si, Chang-Mei [1 ]
Mao, Zhuo-Ya [1 ]
Zhou, Wen [1 ]
Molinski, Tadeusz F. [2 ,3 ]
Wei, Bang-Guo [1 ]
Lin, Guo-Qiang [1 ]
机构
[1] Fudan Univ, Sch Pharm, Dept Nat Prod Chem, 826 Zhangheng Rd, Shanghai 201203, Peoples R China
[2] Univ Calif San Diego, Dept Chem & Biochem, 9500 Gilman Dr, La Jolla, CA 92093 USA
[3] Univ Calif San Diego, Skaggs Sch Pharm & Pharmaceut Sci, 9500 Gilman Dr, La Jolla, CA 92093 USA
来源
ORGANIC CHEMISTRY FRONTIERS | 2017年 / 4卷 / 06期
基金
美国国家卫生研究院; 中国博士后科学基金; 中国国家自然科学基金;
关键词
MARINE CYCLIC DEPSIPEPTIDE; ASYMMETRIC-SYNTHESIS; ANTIMALARIAL ACTIVITY; PEPTIDE-SYNTHESIS; DOLASTATIN; 10; CYANOBACTERIUM; ANALOG; INHIBITORS; ACIDS; 1-HYDROXY-7-AZABENZOTRIAZOLE;
D O I
10.1039/c7qo00052a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Symplocin A, a linear peptide possessing N-terminal N, N-dimethylisoleucine, statine, and valic acid residues, has been synthesized for the first time employing our previously established 'one-pot intramolecular tandem protocol'. Moreover, the stereochemistry of natural symplocin A was unambiguously revised through the confirmation by 1D NMR, 2D NMR, and HPLC comparisons with an authentic natural product.
引用
收藏
页码:995 / 1004
页数:10
相关论文
共 48 条
  • [1] Cyclic Lipodepsipeptides in Novel Antimicrobial Drug Discovery
    Bionda, Nina
    Cudic, Predrag
    [J]. CROATICA CHEMICA ACTA, 2011, 84 (02) : 315 - 329
  • [2] EFFECT OF TERTIARY BASES ON O-BENZOTRIAZOLYLURONIUM SALT-INDUCED PEPTIDE SEGMENT COUPLING
    CARPINO, LA
    EL-FAHAM, A
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (04) : 695 - 698
  • [3] EFFICIENCY IN PEPTIDE COUPLING - 1-HYDROXY-7-AZABENZOTRIAZOLE VS 3,4-DIHYDRO-3-HYDROXY-4-OXO-1,2,3-BENZOTRIAZINE
    CARPINO, LA
    EL-FAHAM, A
    ALBERICIO, F
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (11) : 3561 - 3564
  • [4] RACEMIZATION STUDIES DURING SOLID-PHASE PEPTIDE-SYNTHESIS USING AZABENZOTRIAZOLE-BASED COUPLING REAGENTS
    CARPINO, LA
    EL-FAHAM, A
    ALBERICIO, F
    [J]. TETRAHEDRON LETTERS, 1994, 35 (15) : 2279 - 2282
  • [5] 1-HYDROXY-7-AZABENZOTRIAZOLE - AN EFFICIENT PEPTIDE COUPLING ADDITIVE
    CARPINO, LA
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (10) : 4397 - 4398
  • [6] N-METHYLAMINO ACIDS IN PEPTIDE-SYNTHESIS .5. SYNTHESIS OF N-TERT-BUTYLOXYCARBONYL, N-METHYLAMINO ACIDS BY N-METHYLATION
    CHEUNG, ST
    BENOITON, NL
    [J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1977, 55 (05): : 906 - 910
  • [7] Total Synthesis, Stereochemical Assignment, and Antimalarial Activity of Gallinamide A
    Conroy, Trent
    Guo, Jin T.
    Linington, Roger G.
    Hunt, Nicholas H.
    Payne, Richard J.
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (48) : 13544 - 13552
  • [8] Total Synthesis, and Antimalarial Activity of Symplostatin 4
    Conroy, Trent
    Guo, Jin T.
    Hunt, Nicholas H.
    Payne, Richard J.
    [J]. ORGANIC LETTERS, 2010, 12 (23) : 5576 - 5579
  • [9] The antibody-drug conjugate: an enabling modality for natural product-based cancer therapeutics
    Gerber, Hans-Peter
    Koehn, Frank E.
    Abraham, Robert T.
    [J]. NATURAL PRODUCT REPORTS, 2013, 30 (05) : 625 - 639
  • [10] Caldoramide, a Modified Pentapeptide from the Marine Cyanobacterium Caldora penicillata
    Gunasekera, Sarath P.
    Imperial, Lorelie
    Garst, Christiana
    Ratnayake, Ranjala
    Dang, Long H.
    Paul, Valerie J.
    Luesch, Hendrik
    [J]. JOURNAL OF NATURAL PRODUCTS, 2016, 79 (07): : 1867 - 1871