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Literature DB >> 6938990

Biosynthesis of vitamin B12: identity of fragment extruded during ring contraction to the corrin macrocycle.

A R Battersby, M J Bushell, C Jones, N G Lewis, A Pfenninger.

Abstract

Incorporation experiments with labeled sirohydrochlorin and trimethylisobacteriochlorin demonstrate that ring contraction in vivo to the corrin macrocycle of vitamin B12 liberates acetic acid. The C-20 atom of the precursors becomes the acetate carboxyl carbon.

Entities: Chemical

Mesh：

Substances：

Year: 1981 PMID： 6938990 PMCID： PMC318978 DOI： 10.1073/pnas.78.1.13

Source DB: PubMed Journal: Proc Natl Acad Sci U S A ISSN： 0027-8424 Impact factor: 11.205

5 in total

1. Alkaloid biosynthesis. XII. The biosynthesis of narcotine.

Authors: A R Battersby; M Hirst; D J McCaldin; R Southgate; J Staunton
Journal: J Chem Soc Perkin 1 Date: 1968

2. Biosynthesis of porphyrins and related macrocycles. Part 10. Vitamin B12: biochemical derivation of cobyrinic acid from uroporphyrinogen III. Studies with corresponding ring c methyl heptacarboxylic prophyrinogen, and proof of seven intact methyl transfers.

Authors: A R Battersby; E McDonald; R Hollenstein; M Ihara; F Satoh; D C Williams
Journal: J Chem Soc Perkin 1 Date: 1977

3. Biosynthesis of vitamin B12: mode of incorporation of factor III into cobyrinic acid.

Authors: C Nussbaumer; M Imfeld; G Wörner; G Müller; D Arigoni
Journal: Proc Natl Acad Sci U S A Date: 1981-01 Impact factor: 11.205

4. [On the preparation of intermediates in cobyrinic acid biosynthesis by suspensions of Propionibacterium shermanii (author's transl)].

Authors: K H Bergmann; R Deeg; K D Gneuss; H P Kriemler; G Müller
Journal: Hoppe Seylers Z Physiol Chem Date: 1977-10

5. Ring contraction of hydroporphinoid to corrinoid complexes.

Authors: V Rasetti; A Pfaltz; C Kratky; A Eschenmoser
Journal: Proc Natl Acad Sci U S A Date: 1981-01 Impact factor: 11.205

5 in total

11 in total

Review 1. Algae need their vitamins.

Authors: Martin T Croft; Martin J Warren; Alison G Smith
Journal: Eukaryot Cell Date: 2006-08

2. Biosynthesis of vitamin B12: factor IV, a new intermediate in the anaerobic pathway.

Authors: A I Scott; N J Stolowich; J Wang; O Gawatz; E Fridrich; G Müller
Journal: Proc Natl Acad Sci U S A Date: 1996-12-10 Impact factor: 11.205

3. 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

4. Biosynthesis of vitamin B12: nature of the volatile fragment generated during formation of the corrin ring system.

Authors: L Mombelli; C Nussbaumer; H Weber; G Müller; D Arigoni
Journal: Proc Natl Acad Sci U S A Date: 1981-01 Impact factor: 11.205

5. Biosynthesis of vitamin B12: isolation of precorrin-6x, a metal-free precursor of the corrin macrocycle retaining five S-adenosylmethionine-derived peripheral methyl groups.

Authors: D Thibaut; L Debussche; F Blanche
Journal: Proc Natl Acad Sci U S A Date: 1990-11 Impact factor: 11.205

Biosynthesis of vitamin B12: identity of fragment extruded during ring contraction to the corrin macrocycle.

1. Alkaloid biosynthesis. XII. The biosynthesis of narcotine.

2. Biosynthesis of porphyrins and related macrocycles. Part 10. Vitamin B12: biochemical derivation of cobyrinic acid from uroporphyrinogen III. Studies with corresponding ring c methyl heptacarboxylic prophyrinogen, and proof of seven intact methyl transfers.

3. Biosynthesis of vitamin B12: mode of incorporation of factor III into cobyrinic acid.

4. [On the preparation of intermediates in cobyrinic acid biosynthesis by suspensions of Propionibacterium shermanii (author's transl)].

5. Ring contraction of hydroporphinoid to corrinoid complexes.

Review 1. Algae need their vitamins.

2. Biosynthesis of vitamin B12: factor IV, a new intermediate in the anaerobic pathway.

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

4. Biosynthesis of vitamin B12: nature of the volatile fragment generated during formation of the corrin ring system.

5. Biosynthesis of vitamin B12: isolation of precorrin-6x, a metal-free precursor of the corrin macrocycle retaining five S-adenosylmethionine-derived peripheral methyl groups.

6. Biosynthesis of vitamin B12: structure of precorrin-6x octamethyl ester.

7. Regulation of cobalamin biosynthetic operons in Salmonella typhimurium.

8. Bactobilin: blue bile pigment isolated from Clostridium tetanomorphum.

9. Biosynthesis of vitamin B12: concerning the origin of the methine protons of the corrin nucleus.

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