Tetrapyrrole biosynthesis

The biosynthesis of the tetrapyrrole macrocycle and its branches leading to haem and chlorophylls has been covered in detail in several reviews - - and will be concisely described in this section. Tetrapyrrole biosynthesis occurs entirely in the plastids and is composed of several enzymatic steps starting from 5-aminolevulinic acid (ALA), which is the key precursor of porphyrins and the source of their carbon and nitrogen. 

Lascelles, June Tetrapyrrole Biosynthesis and Its Regulation. New York W. A. Benjamin 1964. 

E. McDonald, Biosynthesis of the pigments of life Formation of the macrocycle. Nature 285 17, 1980. This paper discusses the steps in tetrapyrrole biosynthesis and the pathways diverting this nucleus to chlorophylls, hemes, cytochromes, and other macrocyclic pigments. 

Tanaka R, Tanaka A. Tetrapyrrole biosynthesis in higher plants. 

Vevodova J, Graham RM, Raux E, Schubert HL, Roper Dl, Brindley AA, et al. Structure/function studies on a S-adenosyl-L-methionine-dependent uroporphyrinogen 111 C methyltransferase (SUMT), a key regulatory enzyme of tetrapyrrole biosynthesis. J. Mol. Biol. 2004 344 419-433. 

Leeper, F.J., and Rock, M., Modified substrates for tetrapyrrole biosynthesis. Analogues of porphobilinogen showing unusual inhibition of porphobilinogen deaminase, 7. Chem. Soc., Chem. Commun., 242, 1992. 

Wakao N, Yokoi N, Isoyama N, Hiraishi A, Shimada K, Kobayashi M, Kise H, Iwaki M, Itoh S, Takaichi S, Sakurai Y (1996) Discovery of natural photosynthesis using Zn-containing bacte-riochlorophyll in aerobic bacterium Acidiphilum rubrum. Plant Cell Physiol 37 889-893 Warren MJ, Bolt E, Woodcock SC (1994) 5-Aminolaevulinic acid synthase and uroporphyrinogen methylase two control enzymes of tetrapyrrole biosynthesis and modification. In Biosynthesis of the tetrapyrrole pigments (Ciba foundation symposium 180). Wiley, Chichester, pp 26—40... 

B. Franck, C. Wegner, and G. Bringman, Tetrapyrrole biosynthesis. 9. Synthesis of protected norand homo-porphobilinogen, Z./ eWgs A/w. Chem., 253 (1980). 

G. Bringmarm and B. Franck, Tetrapyrrole biosynthesis 14 Extremely selective porphyrin formation by cyclisation of different oligopynoles," Liebigs Ann. Chem. 1272 (1982). 

Biosynthesis synthesis The biosynthesis of H. dj has not yet been clarified however, because of the substitution pattern it may be assumed that H. d, is formed by the usual tetrapyrrole biosynthesis route and that the methyl groups in the 2- and 7-positions originate from 5-adenosylmethionine. Total syntheses of por-phyrin d have been carried out in several laboratories and the configuration of H. d) has also be determined. Lit. Chem. Rev. 94, 327 (1994) ). Chem. Soc., Chem. Com-mun. 1993, 277. - Synthesis J. Am. Chem. Soc. 109, 3149 (1987) J. Chem. Soc., Perkin Trans. 1 1997,2111,2123 Tetrahedron Lett. 33, 765 (1992). - [CAS 59948-35-51... 

Propionic acid bacteria can synthesize a number of tetrapyrrole compounds corrinoids, heme, heme-containing enzymes, cytochromes, and linear tetrapyrroles. Biosynthesis of tetrapyrroles by all microorganisms starts with the formation of 5-aminolevulinic acid (ALA) (Corcoran and Shemin, 1957) and proceeds through the formation of porphobilinogen (PBG) and uroporphyrinogen (UPB) (Fig. 4.19A). Of the four possible isomers of uroporphyrinogenes, only the derivatives of UPB III are found in nature. 

Figure 5.6. Outline of tetrapyrrole biosynthesis from ALA. For further detail, see Ref. 27.

Rebeiz and co-workers have attempted to develop the use of ALA and chlorophyll biosynthesis modulators as photodynamic herbicides/ " This novel approach makes use of the fact that the biosynthesis of ALA appears to be the rate-limiting step in tetrapyrrole biosynthesis. The application of ALA circumvents this rate-limiting step, and treated plant tissues accumulate tetrapyrroles, which can act as photodynamic herbicides and induce phytotoxicity similar to that now established for NDPEs. The susceptibility of treated plants is dependent on the nature of the tetrapyrroles that accumulate. " ... 

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