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
来源：
ARKIVOC | 2005年
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
  • [41] STRUCTURE-ACTIVITY RELATIONSHIP OF A BITTER DIKETOPIPERAZINE REVISITED
    GOODMAN, M
    TEMUSSI, PA
    BIOPOLYMERS, 1985, 24 (08) : 1629 - 1633
  • [42] Studies on Structure and Biological Activity of Indole Diketopiperazine Alkaloids
    Jia, Bin
    Ma, Yangmin
    Chen, Di
    Chen, Pu
    Hu, Yan
    PROGRESS IN CHEMISTRY, 2018, 30 (08) : 1067 - 1081
  • [43] N-methylphenylalanyl-dehydrobutyrine diketopiperazine, an A-factor mimic that restores antibiotic biosynthesis and morphogenesis in Streptomyces globisporus 1912-B2 and Streptomyces griseus 1439
    Matselyukh, Bohdan
    Mohammadipanah, Fatemeh
    Laatsch, Hartmut
    Rohr, Juergen
    Efremenkova, Olga
    Khilya, Volodymyr
    JOURNAL OF ANTIBIOTICS, 2015, 68 (01): : 9 - 14
  • [44] CRYSTAL STRUCTURE OF N,N'-DIMETHYL-DIKETOPIPERAZINE
    GROTH, P
    ACTA CHEMICA SCANDINAVICA, 1969, 23 (09): : 3155 - &
  • [45] CRYSTAL-STRUCTURE OF BISGLYCINE HYDROBROMIDE - A REINVESTIGATION
    NATARAJAN, S
    ZANGRANDO, E
    PROCEEDINGS OF THE INDIAN ACADEMY OF SCIENCES-CHEMICAL SCIENCES, 1992, 104 (04): : 483 - 487
  • [46] REINVESTIGATION OF STRUCTURE OF PINASTRIC ACID + ISOPINASTRIC ACID
    AGARWAL, SC
    SESHADRI, TR
    INDIAN JOURNAL OF CHEMISTRY, 1964, 2 (01): : 17 - &
  • [47] Reinvestigation of the structure of Brucella O-antigens
    Kubler-Kielb, Joanna
    Vinogradov, Evgeny
    CARBOHYDRATE RESEARCH, 2013, 378 : 144 - 147
  • [48] REINVESTIGATION OF STRUCTURE OF PERFLUOROETHANE BY ELECTRON-DIFFRACTION
    GALLAHER, KL
    YOKOZEKI, A
    BAUER, SH
    JOURNAL OF PHYSICAL CHEMISTRY, 1974, 78 (23): : 2389 - 2395
  • [49] A REINVESTIGATION OF STRUCTURE OF INDOPHENINE - SOME NEW EVIDENCE
    BALLANTINE, JA
    FENWICK, RG
    JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1970, (16): : 2264 - +
  • [50] REINVESTIGATION OF SPERMATIC FLAGELLA STRUCTURE - THE TELEOSTEAN CYPRINODONTIDAE
    THIAW, OT
    MATTEI, X
    ROMAND, R
    MARCHAND, B
    JOURNAL OF ULTRASTRUCTURE AND MOLECULAR STRUCTURE RESEARCH, 1986, 97 (1-3): : 109 - 118
12345