Complete N-1 regiocontrol in the formation of N-arylimidazoles.: Synthesis of the active site His-Tyr side chain coupled dipeptide of cytochrome c oxidase

被引:80
作者
Elliott, GI [1 ]
Konopelski, JP [1 ]
机构
[1] Univ Calif Santa Cruz, Dept Chem & Biochem, Santa Cruz, CA 95064 USA
关键词
D O I
10.1021/ol006271w
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] Under catalysis by copper(II) acetate, complete regiocontrol (N-1 versus N-3) was obtained in the arylation of substituted imidazoles with aryllead(IV) reagents. The mildness of the reaction conditions (rt, no added base) allows for the first synthesis of the histidine-tyrosine side chain coupled dipeptide found in the active site of cytochrome c oxidase.
引用
收藏
页码:3055 / 3057
页数:3
相关论文
共 37 条
  • [1] SYNTHESIS OF N-EPSILON-(P-BROMOPHENYL)-L-LYSINE AND N-TAU-(P-BROMOPHENYL)-L-HISTIDINE AS MODELS FOR ADDUCTS OF BROMOBENZENE 3,4-OXIDE TO PROTEIN - OBSERVATION OF AN UNUSUAL PD-CATALYZED N-TAU-ARYL TO N-PI-ARYL SUBSTITUENT MIGRATION
    BAMBAL, R
    HANZLIK, RP
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (04) : 729 - 732
  • [2] ARYLLEAD TRIACETATES - REGIOSELECTIVE REAGENTS FOR N-ARYLATION OF AMINES
    BARTON, DHR
    DONNELLY, DMX
    FINET, JP
    GUIRY, PJ
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (09): : 2095 - 2012
  • [3] On the structure and reaction with pyridine of o-methoxyphenyllead acetates
    Buston, JEH
    Compton, RG
    Leech, MA
    Moloney, MG
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1999, 585 (02) : 326 - 330
  • [4] CARGANICO G, 1991, FARMACO, V46, P209
  • [5] ENANTIOMERICALLY PURE DIHYDROPYRIMIDINONES AS REAGENTS AND AUXILIARIES FOR ASYMMETRIC-SYNTHESIS
    CHU, KS
    NEGRETE, GR
    KONOPELSKI, JP
    LAKNER, FJ
    WOO, NT
    OLMSTEAD, MM
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (05) : 1800 - 1812
  • [6] An efficient diamine copper complex-catalyzed coupling of arylboronic acids with imidazoles
    Collman, JP
    Zhong, M
    [J]. ORGANIC LETTERS, 2000, 2 (09) : 1233 - 1236
  • [7] Close structural analogues of the cytochrome c oxidase Fea3/CuB center show clean 4e- electroreduction of O2 to H2O at physiological pH
    Collman, JP
    Rapta, M
    Bröring, M
    Raptova, L
    Schwenninger, R
    Boitrel, B
    Fu, L
    L'Her, M
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (06) : 1387 - 1388
  • [8] Syntheses and pKa determination of 1-(o-hydroxyphenyl)imidazole carboxylic esters
    Collman, JP
    Wang, Z
    Zhong, M
    Zeng, L
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (08): : 1217 - 1221
  • [9] IMIDAZOL-1-YL AND PYRIDIN-3-YL DERIVATIVES OF 4-PHENYL-1,4-DIHYDROPYRIDINES COMBINING CA2+ ANTAGONISM AND THROMBOXANE-A(2) SYNTHASE INHIBITION
    COZZI, P
    CARGANICO, G
    FUSAR, D
    GROSSONI, M
    MENICHINCHERI, M
    PINCIROLI, V
    TONANI, R
    VAGHI, F
    SALVATI, P
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1993, 36 (20) : 2964 - 2972
  • [10] Palladium-catalyzed coupling of vinylogous amides with aryl halides: Applications to the synthesis of heterocycles
    Edmondson, SD
    Mastracchio, A
    Parmee, ER
    [J]. ORGANIC LETTERS, 2000, 2 (08) : 1109 - 1112