TY - JOUR
T1 - Preparation of Fe4S4 iron-sulphur protein analogues with hydrophobic macrocyclic tetrathiol ligand anchored to a 38-membered cyclophane type skeleton
AU - Uoto, Kouichi
AU - Tomohiro, Takenori
AU - Okuno, Hiroaki (Yohmei)
PY - 1990/4/2
Y1 - 1990/4/2
N2 - The preparation of Fe4S4 cubane type active site analogues for iron-sulphur proteins in which the active core is surrounded by an intramolecular hydrophobic domain formed by a 38-membered ring consisting of a cyclophane skeleton is described. An efficient synthesis of the macrocyclic tetrathiol ligands, bis[N,N-bis(4-mercaptobenzoyl)-N, N′-octamethylene- 4,4′-diaminodiphenylmethane] (3a), bis- N,N′-bis {4-(mercaptomethyl)benzoyl}-N, N′-octamethylene -4,4′-diaminodiphenylmethane](3b) and bis[N,N′-bis(3-mercapto-3-methylbutanoyl0)-N, N′-octamethyleneN,N′- octamethylene-4,4′-diaminodiphenylmethane] (3c) is achieved. Reaction of the cyclic tetrathiol ligand 3 with [Fe4S4(SBut)4]2-(1c) afforded [Fe4S4{cycl- (XN-p-C6a-H4-p-CH2-C6 H4-XN[CH2]8)2}]2- [X = p- SC6H4CO(2a), p-SCH2C6H4CO(2b), SC(CH3)2- CH2CO(2c)]. Thus the new clusters embedded in the cyclophane environment are obtained in good yields (70-90%) as black powders with melting points >300°C. They dissolve in DMF, DMSO and propylene carbonate, but are hardly soluble in most common organic solvents and water.
AB - The preparation of Fe4S4 cubane type active site analogues for iron-sulphur proteins in which the active core is surrounded by an intramolecular hydrophobic domain formed by a 38-membered ring consisting of a cyclophane skeleton is described. An efficient synthesis of the macrocyclic tetrathiol ligands, bis[N,N-bis(4-mercaptobenzoyl)-N, N′-octamethylene- 4,4′-diaminodiphenylmethane] (3a), bis- N,N′-bis {4-(mercaptomethyl)benzoyl}-N, N′-octamethylene -4,4′-diaminodiphenylmethane](3b) and bis[N,N′-bis(3-mercapto-3-methylbutanoyl0)-N, N′-octamethyleneN,N′- octamethylene-4,4′-diaminodiphenylmethane] (3c) is achieved. Reaction of the cyclic tetrathiol ligand 3 with [Fe4S4(SBut)4]2-(1c) afforded [Fe4S4{cycl- (XN-p-C6a-H4-p-CH2-C6 H4-XN[CH2]8)2}]2- [X = p- SC6H4CO(2a), p-SCH2C6H4CO(2b), SC(CH3)2- CH2CO(2c)]. Thus the new clusters embedded in the cyclophane environment are obtained in good yields (70-90%) as black powders with melting points >300°C. They dissolve in DMF, DMSO and propylene carbonate, but are hardly soluble in most common organic solvents and water.
UR - http://www.scopus.com/inward/record.url?scp=1542280807&partnerID=8YFLogxK
U2 - 10.1016/S0020-1693(00)80418-1
DO - 10.1016/S0020-1693(00)80418-1
M3 - 学術論文
AN - SCOPUS:1542280807
SN - 0020-1693
VL - 170
SP - 123
EP - 127
JO - Inorganica Chimica Acta
JF - Inorganica Chimica Acta
IS - 1
ER -