A regioselective synthesis of the dephospho ditholene protected molybdopterin

被引：7
作者：
Pimkov, Igor V. [1 ]
Peterson, Antoinette A. [1 ]
Vaccarello, David N. [1 ]
Basu, Partha [1 ]
机构：
[1] Duquesne Univ, Dept Chem & Biochem, Pittsburgh, PA 15282 USA
来源：
RSC ADVANCES | 2014年 / 4卷 / 37期
基金：
美国国家卫生研究院; 美国国家科学基金会;
关键词：
MOLYBDENUM COFACTOR; REGIOSPECIFIC SYNTHESIS; ENZYMES; SPECTROSCOPY; COMPLEXES; CENTERS; DESIGN; MODEL;
D O I：
10.1039/c4ra02786h
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The molybdopterin (MPT) is a complex molecule, made out of three distinctly different components. A retrosynthetic analysis provides a possible route for its synthesis that utilizes the coupling of a diamine with an osone analog. A regioselective condensation of the diamine with an osone affords the dephospho MPT, which has been characterized by NMR and IR spectroscopies, as well as highresolution mass spectrometry.
引用
收藏
页码：19072 / 19076
页数：5
相关论文
共 39 条
  • [1] PTERIDINE CHEMISTRY .10. METHYLATION STUDIES .3. STERIC EFFECTS OF PHENYL GROUPS AT C-6 AND C-7
    ANGIER, RB
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1963, 28 (06) : 1509 - &
  • [2] Syntheses, spectroscopy, and redox chemistry of encapsulated Oxo-Mo(V) centers: Implications for pyranopterin-containing molybdoenzymes
    Basu, P
    Nemykin, VN
    Sengar, RS
    [J]. INORGANIC CHEMISTRY, 2003, 42 (23) : 7489 - 7501
  • [3] Pterin chemistry and its relationship to the molybdenum cofactor
    Basu, Partha
    Burgmayer, Sharon J. N.
    [J]. COORDINATION CHEMISTRY REVIEWS, 2011, 255 (9-10) : 1016 - 1038
  • [4] Synthesis of the organic ligand of the molybdenum cofactor, in protected form
    Bradshaw, B
    Dinsmore, A
    Ajana, W
    Collison, D
    Garner, CD
    Joule, JA
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (24): : 3239 - 3244
  • [5] The synthesis of pyrano[2,3-b]quinoxalines related to molybdopterin
    Bradshaw, B
    Dinsmore, A
    Collison, D
    Garner, CD
    Joule, JA
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (24): : 3232 - 3238
  • [6] Synthesis of Cyclic Pyranopterin Monophosphate, a Biosynthetic Intermediate in the Molybdenum Cofactor Pathway
    Clinch, Keith
    Watt, Derek K.
    Dixon, Rachel A.
    Baars, Sylvia M.
    Gainsford, Graeme J.
    Tiwari, Ashish
    Schwarz, Guenter
    Saotome, Yas
    Storek, Michael
    Belaidi, Abdel A.
    Santamaria-Araujo, Jose A.
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2013, 56 (04) : 1730 - 1738
  • [7] COREY EJ, 1972, TETRAHEDRON LETT, P3769
  • [8] REACTIONS OF ETHYLENE OXIDES .1. PREPARATION OF ETHYLENE SULPHIDES AND TRITHIOCARBONATES
    CULVENOR, CCJ
    DAVIES, W
    PAUSACKER, KH
    [J]. JOURNAL OF THE CHEMICAL SOCIETY, 1946, (NOV): : 1050 - 1052
  • [9] A chemical approach to systematically designate the pyranopterin centers of molybdenum and tungsten enzymes and synthetic models
    Fischer, B
    Enemark, JH
    Basu, P
    [J]. JOURNAL OF INORGANIC BIOCHEMISTRY, 1998, 72 (1-2) : 13 - 21
  • [10] Gabriel S., 1901, CHEM BER, V34, P1234
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