Diazo ester insertion in N-H bonds of amino acid derivatives and insulin catalyzed by water-soluble iron and ruthenium porphyrin complexes (FeTSPPCl) as application of carbenoid transfer in aqueous media

被引:21
作者
Srour, Hassan F. [1 ]
Le Maux, Paul [1 ]
Chevance, Soizic [1 ]
Carrie, Daniel [1 ]
Le Yondre, Nicolas [2 ]
Simonneaux, Gerard [1 ]
机构
[1] Univ Rennes 1, Inst Sci Chim Rennes, UMR 6226, F-35042 Rennes, France
[2] Univ Rennes 1, CRMPO, F-35042 Rennes, France
关键词
Catalytic NH insertion; Iron porphyrin; Diazo ester; Amino ester; Insulin; RHODIUM CARBENOIDS; ETHYL DIAZOACETATE; CYCLOPROPANATION; DIAZOMETHYLPHOSPHONATE; METALLOPORPHYRINS; BIOCONJUGATION; YLIDES;
D O I
10.1016/j.molcata.2015.06.028
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
The metal complex FeTSPPCl (5,10,15,20-tetrakis)-(4-sulfonato-phenyl)-porphyrin-iron(III) chloride is an active catalyst for carbenoid insertion in N-H bonds of aminoacid derivatives in aqueous media. A variety of diazoacetates and methyl diazophosphonate were used as carbenoid precursors. The commercially available iron porphyrin complex can also selectively catalyze allcylation of the N-terminus of insulin (chain B). (C) 2015 Elsevier B.V. All rights reserved.
引用
收藏
页码:194 / 203
页数:10
相关论文
共 39 条
  • [1] N-H insertion reactions of rhodium carbenoids .1. Preparation of alpha-amino acid and alpha-aminophosphonic acid derivatives
    Aller, E
    Buck, RT
    Drysdale, MJ
    Ferris, L
    Haigh, D
    Moody, CJ
    Pearson, ND
    Sanghera, JB
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (24): : 2879 - 2884
  • [2] Selective tryptophan modification with rhodium carbenoids in aqueous solution
    Antos, JM
    Francis, MB
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (33) : 10256 - 10257
  • [3] Transition metal catalyzed methods for site-selective protein modification
    Antos, John M.
    Francis, Matthew B.
    [J]. CURRENT OPINION IN CHEMICAL BIOLOGY, 2006, 10 (03) : 253 - 262
  • [4] Chemoselective Tryptophan Labeling with Rhodium Carbenoids at Mild pH
    Antos, John M.
    McFarland, Jesse M.
    Iavarone, Anthony T.
    Francis, Matthew B.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (17) : 6301 - 6308
  • [5] Iron corroles and porphyrins as very efficient and highly selective catalysts for the reactions of α-diazo esters with amines
    Aviv, I
    Gross, Z
    [J]. SYNLETT, 2006, (06) : 951 - 953
  • [6] Iron(III) corroles and porphyrins as superior catalysts for the reactions of diazoacetates with nitrogen- or sulfur-containing nucleophilic substrates: Synthetic uses and mechanistic insights
    Aviv, Iris
    Gross, Zeev
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (13) : 3995 - 4005
  • [7] Iron porphyrins catalyze the synthesis of non-protected amino acid esters from ammonia and diazoacetates
    Aviv, Iris
    Gross, Zeev
    [J]. CHEMICAL COMMUNICATIONS, 2006, (43) : 4477 - 4479
  • [8] Iron porphyrin catalyzed N-H insertion reactions with ethyl diazoacetate
    Baumann, Lynnette K.
    Mbuvi, Harun M.
    Du, Guodong
    Woo, L. Keith
    [J]. ORGANOMETALLICS, 2007, 26 (16) : 3995 - 4002
  • [9] Iron(III)-porphyrin Complex FeTSPP: A Versatile Water-soluble Catalyst for Oxidations in Organic Syntheses, Biorenewables Degradation and Environmental Applications
    boehm, Philipp
    Groeger, Harald
    [J]. CHEMCATCHEM, 2015, 7 (01) : 22 - 28
  • [10] Buck RT, 2000, CHEM-EUR J, V6, P2160, DOI 10.1002/1521-3765(20000616)6:12<2160::AID-CHEM2160>3.3.CO