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Synthetic and biosynthetic studies on vitamin B12


, : Synthetic and biosynthetic studies on vitamin B12. Journal of Natural Products 51(4): 643-661

Research into synthesis and biosynthesis of vitamin B-12 involving skills at microscale level, is described.

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Accession: 001962673

PMID: 3062132

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Related references

Battersby, A.R.; Reiter, L.A., 1984: Synthetic studies relevant to biosynthetic research on vitamin b 12 3. an approach to isobacteriochlorins via nitrones. 2,2,8,8,12,13,17,18-Octamethylisobacteriochlorin was synthesized in modest yield by a route which makes use of the chemistry of nitrones to build a linear system which is cyclized using Cu(II) acetate.

Battersby, A.R.; Westwood, S.W., 1987: Synthetic studies relevant to biosynthetic research on vitamin b 12 part 5. synthesis of rs ring b imide. Future biosynthetic research on vitamin B12 depends on the synthesis of a family of isobacteriochlorin pigments. A key building block required for this work is 2-(2-methoxycarbonylethyl)-3-methoxycarbonylmethyl-3-methylsuccinimide, usually called...

Battersby, A.R.; Fookes, C.J.R.; Snow, R.J., 1984: Synthetic studies relevant to biosynthetic research on vitamin b 12 2. syntheses of c methylated chlorins via lactams. C-Methylated chlorins were synthesized by 2 approaches. For one, ring-B and ring-C of the final chlorin were built sequentially onto a thiolactam system which acted as the A-D component. The preferred alternative method involved joining together a...

Arnott, D.M.; Harrison, P.J.; Henderson, G.B.; Sheng, Z.C.; Leeper, F.J.; Battersby, A.R., 1989: Synthetic studies relevant to biosynthetic research on vitamin b 12 part 9. synthesis of 20 methyl and 20 cyanoisobacteriochlorins. Isobacteriochlorins carrying a C-methyl group at C-20 of the macrocycle are important for research on the biosynthesis of vitamin B12. Several different approaches are studied which allow the introducton of a C-20 methyl group into model isobacter...

Harrison, P.J.; Sheng, Z.C.; Fookes, C.J.R.; Battersby, A.R., 1987: Synthetic studies relevant to biosynthetic research on vitamin b 12 part 4. development of the photochemical route to isobacteriochlorins. Pigments based on the isobacteriochlorin macrocyle are of great importance for research on the biosynthesis of vitamin B12. A synthesis of the isobacteriochlorin ring system is developed in which a key step is an 18.pi.-photochemical cyclisation....

Battersby, A.R.; Dutton, C.J.; Fookes, C.J.R.; Turner, S.P.D., 1988: Synthetic studies relevant to biosynthetic research on vitamin b 12 part 6. synthesis of chlorins by a photochemical approach. A rational synthetic route to C-methylated chlorins has been developed in which a seco-chlorin is constructed and then cyclised photochemically by an 18.pi.-electrocyclic process. The conditions of the synthesis are mild and are compatible with th...

Battersby, A.R.; Turner, S.P.D.; Block, M.H.; Sheng, Z.C.; Zimmerman, S.C., 1988: Synthetic studies relevant to biosynthetic research on vitamin b 12 part 8. synthesis of racemic faktor i octamethyl ester. Several variations have been explored of the general synthesis of chlorins which uses a photochemical ring-closure of the macrocycle as the key step. This work leads to a synthesis of (.+-.)-Faktor-l octamethyl ester, a chlorin which arises, in th...

Battersby, A.R.; Fookes, C.J.R.; Snow, R.J., 1984: Synthetic studies relevant to biosynthetic research on vitamin b 12 1. syntheses of c methylated chlorins based on 1 pyrrolines 3 4 dihydropyrroles. Two routes are explored for the synthesis of chlorins geminally substituted in the reduced ring; both involve cyclizations of 1-pyrroline (3,4-dihydropyrrole) systems promoted by Cu(II) salts. In the preferred synthesis, a pyrrolomethyl-1-pyrrolin...

Battersby, A.R.; Dutton, C.J.; Fookes, C.J.R., 1988: Synthetic studies relevant to biosynthetic research on vitamin b 12 part 7. synthesis of racemic bonellin dimethyl ester. The dimethyl ester of the green marine pigment, bonellin, has been synthesized in racemic form by a rational photochemical route. The two proprionate residues of this biologically active pigment have been introduced synthetically in differentiate...

Battersby, A., R.; Block, M., H.; Fookes, C., J.R.; Harrison, P., J.; Henderson, G., B.; Leeper, F., J., 1992: Synthetic studies relevant to biosynthetic research on vitamin B-12: Part 10. Construction of the east and west building blocks for synthesis of isobacteriochlorins. Studies with model compounds have led to the development of effective methods for (a) linking the pyrrolic rings to the reduced rings present in the isobacteriochlorin system (e.g. 4) and (b) for introducing the carbon at C-5 required to complete...