An expeditious synthesis of tailed tren-capped porphyrins

被引:9
作者
Even, P [1 ]
Ruzié, C [1 ]
Ricard, D [1 ]
Boitrel, B [1 ]
机构
[1] Univ Rennes 1, Inst Chim, UMR CNRS 6509, F-35042 Rennes, France
关键词
D O I
10.1021/ol0513802
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
graph A one-pot two-step versatile synthesis of tailed tren-capped porphyrins has been achieved. The two resulting ligands demonstrate that this expeditious method can be applied to various axial bases to obtain highly functionalized macromolecules attractive for heme modeling purposes. Dioxygen binding of the pyridine-tailed iron complex is reported as a direct application.
引用
收藏
页码:4325 / 4328
页数:4
相关论文
共 31 条
[1]   Synthesis and characterization of a new series of potential hemoprotein analogues: "Arbor" porphyrins [J].
Andrioletti, B ;
Boitrel, B ;
Guilard, R .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (04) :1312-1314
[2]   Functional analogues of cytochrome c oxidase, myoglobin, and hemoglobin [J].
Collman, JP ;
Boulatov, R ;
Sunderland, CJ ;
Fu, L .
CHEMICAL REVIEWS, 2004, 104 (02) :561-588
[3]   The chloroacetamido group as a new linker for the synthesis of hemoprotein analogues [J].
Collman, JP ;
Boitrel, B ;
Fu, L ;
Galanter, J ;
Straumanis, A ;
Rapta, M .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (08) :2308-2309
[4]   Isocyanate as a versatile synthon for modular synthesis of functionalized porphyrins [J].
Collman, JP ;
Zhong, W ;
Straumanis, A .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (08) :2424-2425
[5]   CONGRUENT MULTIPLE MICHAEL ADDITION FOR THE SYNTHESIS OF BIOMIMETIC HEME ANALOGS [J].
COLLMAN, JP ;
ZHANG, XM ;
HERRMANN, PC ;
UFFELMAN, ES ;
BOITREL, B ;
STRAUMANIS, A ;
BRAUMAN, JI .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (06) :2681-2682
[6]   Novel protecting strategy for the synthesis of porphyrins with different distal and proximal superstructures [J].
Collman, JP ;
Bröring, M ;
Fu, L ;
Rapta, M ;
Schwenninger, R ;
Straumanis, A .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (23) :8082-8083
[7]   Efficient synthesis of a porphyrin-N-tripod conjugate with covalently linked proximal ligand:: Toward new-generation active-site models of cytochrome c oxidase [J].
Collman, JP ;
Zhong, M ;
Wang, Z ;
Rapta, M ;
Rose, E .
ORGANIC LETTERS, 1999, 1 (13) :2121-2124
[8]   REVERSIBLE OXYGEN ADDUCT FORMATION IN FERROUS COMPLEXES DERIVED FROM A PICKET FENCE PORPHYRIN - MODEL FOR OXYMYOGLOBIN [J].
COLLMAN, JP ;
GAGNE, RR ;
HALBERT, TR ;
MARCHON, JC ;
REED, CA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (23) :7868-7870
[9]   Dioxygen and carbon monoxide binding in dendritic iron(II)porphyrins [J].
Collman, JP ;
Fu, L ;
Zingg, A ;
Diederich, F .
CHEMICAL COMMUNICATIONS, 1997, (02) :193-194
[10]   Aza-crown-capped porphyrin models of myoglobin: Studies of the steric interactions of gas binding [J].
Collman, JP ;
Herrmann, PC ;
Fu, L ;
Eberspacher, TA ;
Eubanks, M ;
Boitrel, B ;
Hayoz, P ;
Zhang, XM ;
Brauman, JI ;
Day, VW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (15) :3481-3489