Deuteroporphyrin IX
IUPAC 名称
3-[20-(2-carboxyethyl)-5,9,14,19-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1,3,5,7,9,11(23),12,14,16,18(21),19-undecaen-4-yl]propanoic acid
描述
Deuteroporphyrin IX is a non-natural dicarboxylic porphyrin. Deuteroporphyrins are porphyrins with four methyl and two propionic acid side chains attached to the pyrrole rings. Deuteroporphyrin IX is described as a fecal porphyrin in patients with endemic chronic arsenic poisoning. (Environmental Sciences (Tokyo, Japan) (2001), 8(6), 561-570.)
Excess accumulation of the biosynthetic intermediate protoporphyrin can lead to extensive tissue damage upon exposure to light since protoporpyhyrin is a potent photosensitizing agent, giving rise to membrane-destroying oxygen radicals or singlet oxygen. For instance, in the human porphyria disease porphyria variegata, a genetic deficiency in a heme biosynthetic enzyme, protoporphyrinogen oxidase, leads to protoporphyrin accumulation and lightdependent skin photosensitivity. Horseradish peroxidase (HRP) in the presence of glutathione (GSH) could oxidize the non-natural porphyrin deuteroporphyrin IX, which is closely related to protoporphyrin IX. The product is a unique green chlorin. One of the pyrrole rings had been modified by addition of an hydroxy and an oxo group, thus giving the characteristic reduced pyrrole ring of the chlorine. Of most importance for human medicine, peroxidative enzymes present in mammalian cells can also carry out these GSH-dependent oxidative conversions of protoporphyrin and deuteroporphyrin. (PMID: 10334939) [HMDB]
异构
CC1=C/C2=C/C3=N/C(=C\C4=C(CCC(O)=O)C(C)=C(N4)/C=C4\N=C(C=C4C)\C=C\1/N\2)/C(CCC(O)=O)=C3C
InChI标识符
InChI=1S/C30H30N4O4/c1-15-9-20-12-25-17(3)21(5-7-29(35)36)27(33-25)14-28-22(6-8-30(37)38)18(4)26(34-28)13-24-16(2)10-19(32-24)11-23(15)31-20/h9-14,31,34H,5-8H2,1-4H3,(H,35,36)(H,37,38)/b19-11-,20-12-,23-11-,24-13-,25-12-,26-13-,27-14-,28-14-
键
KWKUIRGQJJFUCG-LMKUSPAJSA-N