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Exceptional Photochemical Stability of the Co-C Bond of Alkynyl Cobalamins, Potential Antivitamins B12 and Core Elements of B12-Based Biological Vectors.

ABSTRACT: Alkynylcorrinoids are a class of organometallic B12 derivatives, recently rediscovered for use as antivitamins B12 and as core components of B12-based biological vectors. They feature exceptional photochemical and thermal stability of their characteristic extra-short Co-C bond. We describe here the synthesis and structure of 3-hydroxypropynylcobalamin (HOPryCbl) and photochemical experiments with HOPryCbl, as well as of the related alkynylcobalamins: phenylethynylcobalamin and difluoro-phenylethynylcobalamin. Ultrafast spectroscopic studies of the excited state dynamics and mechanism for ground state recovery demonstrate that the Co-C bond of alkynylcobalamins is stable, with the Co-N bond and ring deformations mediating internal conversion and ground state recovery within 100 ps. These studies provide insights required for the rational design of photostable or photolabile B12-based cellular vectors.

SUBMITTER: Salerno EV 

PROVIDER: S-EPMC7201400 | biostudies-literature | 2020 May

REPOSITORIES: biostudies-literature

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Exceptional Photochemical Stability of the Co-C Bond of Alkynyl Cobalamins, Potential Antivitamins B<sub>12</sub> and Core Elements of B<sub>12</sub>-Based Biological Vectors.

Salerno Elvin V EV   Miller Nicholas A NA   Konar Arkaprabha A   Salchner Robert R   Kieninger Christoph C   Wurst Klaus K   Spears Kenneth G KG   Kräutler Bernhard B   Sension Roseanne J RJ  

Inorganic chemistry 20200420 9

Alkynylcorrinoids are a class of organometallic B<sub>12</sub> derivatives, recently rediscovered for use as antivitamins B<sub>12</sub> and as core components of B<sub>12</sub>-based biological vectors. They feature exceptional photochemical and thermal stability of their characteristic extra-short Co-C bond. We describe here the synthesis and structure of 3-hydroxypropynylcobalamin (HOPryCbl) and photochemical experiments with HOPryCbl, as well as of the related alkynylcobalamins: phenylethyny  ...[more]

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