Reinvestigation of tryptophan-dehydrobutyrine diketopiperazine structure

被引:9
|
作者
Avendaño, C [1 ]
Cabezas, N [1 ]
de la Cuesta, E [1 ]
González, JF [1 ]
机构
[1] Univ Complutense, Fac Farm, Dept Quim Organ & Farmaceut, E-28040 Madrid, Spain
关键词
piperazinediones; TDD; N-acetylation; aldol; type condensation;
D O I
10.3998/ark.5550190.0006.905
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Reinvestigation of the title natural product's structure ( 1) has shown the easy racemization of the Trp-stereocenter in some derivatives of cyclo-L-Trp-Gly. The here described synthesis of compound 2, a regioisomer of 1 with the N-methyl group on the nitrogen adjacent to the ethylidene side-chain, permits us to conclude that structure 1 was correct.
引用
收藏
页码:30 / 38
页数:9
相关论文
共 50 条
  • [11] Synthesis of Tryptophan-Based Dimeric Diketopiperazine Alkaloids Using Bioinspired Reactions
    Tadano, Shinji
    Ishikawa, Hayato
    SYNLETT, 2014, 25 (02) : 157 - 162
  • [12] Collective Synthesis and Biological Evaluation of Tryptophan-Based Dimeric Diketopiperazine Alkaloids
    Tadano, Shinji
    Sugimachi, Yukihiro
    Sumimoto, Michinori
    Tsukamoto, Sachiko
    Ishikawa, Hayato
    CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (04) : 1277 - 1291
  • [13] Reinvestigation of the incommensurate structure of αPbO
    Baldinozzi, G
    Raulot, JM
    Petricek, V
    SOLID-STATE CHEMISTRY OF INORGANIC MATERIALS IV, 2003, 755 : 465 - 470
  • [14] REINVESTIGATION OF STRUCTURE OF LOW CRISTOBALITE
    DOLLASE, WA
    ZEITSCHRIFT FUR KRISTALLOGRAPHIE, 1965, 121 (05): : 369 - &
  • [15] A REINVESTIGATION OF STRUCTURE OF CORDYCEPIC ACID
    SPRECHER, M
    SPRINSON, DB
    JOURNAL OF ORGANIC CHEMISTRY, 1963, 28 (09): : 2490 - &
  • [16] STRUCTURE OF ZEYLOXANTHONONE (WIGHTIANONE) - A REINVESTIGATION
    BANERJI, A
    DESHPANDE, AD
    PRADHAN, P
    TETRAHEDRON LETTERS, 1991, 32 (37) : 4995 - 4998
  • [17] A REINVESTIGATION OF CRYSTAL STRUCTURE OF YOOH
    CHRISTENSEN, AN
    ACTA CHEMICA SCANDINAVICA, 1965, 19 (06): : 1504 - +
  • [18] REINVESTIGATION OF STRUCTURE OF CHLORGUANIDE HYDROCHLORIDE
    AMMON, HL
    PLASTAS, LA
    JOURNAL OF MEDICINAL CHEMISTRY, 1973, 16 (02) : 169 - 171
  • [19] STRUCTURE AND PROPERTIES OF 2,5-DIKETOPIPERAZINE
    AUGUSTYNIAK, H
    POSTEPY BIOCHEMII, 1966, 12 (01) : 95 - +
  • [20] N-methylphenylalanyl-dehydrobutyrine diketopiperazine, an A-factor mimic that restores antibiotic biosynthesis and morphogenesis in Streptomyces globisporus 1912-B2 and Streptomyces griseus 1439
    Bohdan Matselyukh
    Fatemeh Mohammadipanah
    Hartmut Laatsch
    Jürgen Rohr
    Olga Efremenkova
    Volodymyr Khilya
    The Journal of Antibiotics, 2015, 68 : 9 - 14