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Cobryketone derived from vitamin B12 via palladium-catalyzed cleavage of the sp3-sp3 carbon-carbon bond.

Cobryketone derived from vitamin B12 via palladium-catalyzed cleavage of the sp3-sp3 carbon-carbon bond.

The Journal of organic chemistry (2013-04-03)

Sylwester Kurcoń, Keith ó Proinsias, Dorota Gryko

ABSTRACT

Heptamethyl cobyrinate was transformed into hexamethyl 8-nor-cobyrinate. The crucial step involved the synthesis of new, vitamin B12 derived cobryketone via palladium-catalyzed cleavage of the sp(3)-sp(3) carbon-carbon bond with the liberation of the ketone. The replacement of sp(3) carbon atom with sp(2) (C═O) at the 8-position produces a bathochromic shift of all absorption bands and makes α and β bands equal as a consequence of the expansion of the existing conjugated system of double bonds.

MATERIALS

Product Number

Brand

Product Description

Sigma-Aldrich

Vitamin B₁₂, BioReagent, suitable for cell culture, suitable for insect cell culture, suitable for plant cell culture, ≥98%

Sigma-Aldrich

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Sigma-Aldrich

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Supelco

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Sigma-Aldrich

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Palladium, wire, diam. 0.5 mm, 99.9% trace metals basis

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Palladium, foil, thickness 1.0 mm, 99.9% trace metals basis

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Palladium, foil, thickness 0.25 mm, 99.98% trace metals basis

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Palladium, sponge, 99.9% trace metals basis

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Palladium, foil, thickness 0.025 mm, 99.9% trace metals basis

Sigma-Aldrich

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Sigma-Aldrich

Palladium, powder, <1 μm, ≥99.9% trace metals basis

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Supelco

Cyanocobalamin (Vitamin B12) solution, 1.0 mg/mL in methanol, ampule of 1 mL, certified reference material, Cerilliant^®

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