Literature DB >> 1731915

Enzymatic synthesis and structure of precorrin-3, a trimethyldipyrrocorphin intermediate in vitamin B12 biosynthesis.

M J Warren1, C A Roessner, S Ozaki, N J Stolowich, P J Santander, A I Scott.   

Abstract

The trimethylated intermediate of vitamin B12 (corrin) biosynthesis, precorrin-3, was produced from various 13C-enriched isotopomers of 5-aminolevulinic acid (ALA), using a multiple-enzyme system containing ALA dehydratase, porphobilinogen deaminase, uro'gen III synthetase, and the S-adenosyl-L-methionine-(SAM)-dependent uro'gen III methyltransferase (M-1) and precorrin-2 methyltransferase (M-2) in the presence of [13C]SAM. Structural analysis of the resulting product, precorrin-3, reveals a close similarity to precorrin-2 but with several subtle differences in the conjugated array of C = C and C = N bonds which reflect the presence of the new C-methyl group at C20 and its influence on the electronic distribution in the dipyrrocorphin chromophore. The implications of this structure for corrin biosynthesis are discussed.

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Year:  1992        PMID： 1731915     DOI： 10.1021/bi00117a043

Source DB:  PubMed          Journal:  Biochemistry        ISSN： 0006-2960            Impact factor:   3.162


  13 in total

1.  Biosynthesis of vitamin B12: concerning the identity of the two-carbon fragment eliminated during anaerobic formation of cobyrinic acid.

Authors:  J Wang; N J Stolowich; P J Santander; J H Park; A I Scott
Journal:  Proc Natl Acad Sci U S A       Date:  1996-12-10       Impact factor: 11.205

2.  Effect of mutations in the transmethylase and dehydrogenase/chelatase domains of sirohaem synthase (CysG) on sirohaem and cobalamin biosynthesis.

Authors:  S C Woodcock; E Raux; F Levillayer; C Thermes; A Rambach; M J Warren
Journal:  Biochem J       Date:  1998-02-15       Impact factor: 3.857

3.  A role for Salmonella typhimurium cbiK in cobalamin (vitamin B12) and siroheme biosynthesis.

Authors:  E Raux; C Thermes; P Heathcote; A Rambach; M J Warren
Journal:  J Bacteriol       Date:  1997-05       Impact factor: 3.490

4.  Biosynthesis of the corrin macrocycle of coenzyme B12 in Pseudomonas denitrificans.

Authors:  L Debussche; D Thibaut; B Cameron; J Crouzet; F Blanche
Journal:  J Bacteriol       Date:  1993-11       Impact factor: 3.490

5.  Gene dissection demonstrates that the Escherichia coli cysG gene encodes a multifunctional protein.

Authors:  M J Warren; E L Bolt; C A Roessner; A I Scott; J B Spencer; S C Woodcock
Journal:  Biochem J       Date:  1994-09-15       Impact factor: 3.857

6.  Biosynthesis of vitamin B12: the preparative multi-enzyme synthesis of precorrin-3A and 20-methylsirohydrochlorin (a 2,7,20-trimethylisobacteriochlorin).

Authors:  N P Stamford; J Crouzet; B Cameron; A I Alanine; A R Pitt; A A Yeliseev; A R Battersby
Journal:  Biochem J       Date:  1996-01-01       Impact factor: 3.857

7.  Evidence for a covalent intermediate in the S-adenosyl-L-methionine-dependent transmethylation reaction catalysed by sirohaem synthase.

Authors:  S C Woodcock; M J Warren
Journal:  Biochem J       Date:  1996-01-15       Impact factor: 3.857

8.  Salmonella typhimurium cobalamin (vitamin B12) biosynthetic genes: functional studies in S. typhimurium and Escherichia coli.

Authors:  E Raux; A Lanois; F Levillayer; M J Warren; E Brody; A Rambach; C Thermes
Journal:  J Bacteriol       Date:  1996-02       Impact factor: 3.490

9.  Cloning, sequencing, and expression of the uroporphyrinogen III methyltransferase cobA gene of Propionibacterium freudenreichii (shermanii).

Authors:  I Sattler; C A Roessner; N J Stolowich; S H Hardin; L W Harris-Haller; N T Yokubaitis; Y Murooka; Y Hashimoto; A I Scott
Journal:  J Bacteriol       Date:  1995-03       Impact factor: 3.490

10.  An enzyme-trap approach allows isolation of intermediates in cobalamin biosynthesis.

Authors:  Evelyne Deery; Susanne Schroeder; Andrew D Lawrence; Samantha L Taylor; Arefeh Seyedarabi; Jitka Waterman; Keith S Wilson; David Brown; Michael A Geeves; Mark J Howard; Richard W Pickersgill; Martin J Warren
Journal:  Nat Chem Biol       Date:  2012-10-07       Impact factor: 15.040
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