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Inorganic cyanide as protecting group in the stereospecific reconstitution of vitamin B12 from an artificial green secocorrinoid


Prieto, Lucas; Neuburger, Markus; Spingler, Bernhard; Zelder, Felix (2016). Inorganic cyanide as protecting group in the stereospecific reconstitution of vitamin B12 from an artificial green secocorrinoid. Organic Letters, 18(20):5292-5295.

Abstract

The synthesis of vitamin B12 in four steps from an artificial green secocorrinoid is presented. The stereospecific
reconstitution of the B-ring of the cobalamin involves a quantitative and rapid ligand-centered radical ring closure reaction leading first to a new B12 derivative with antivitamin activity that is subsequently converted to the natural product. Chemoselectivity in the one-electron reduction of the macrocycle was achieved by introducing inorganic cyanide as an axially coordinating protecting group of the otherwise reduction-sensitive Co(III)-ion. The integrity of structure and function of the reconstituted natural product was unequivocally proven by single crystal structural analysis and a microbiological assay using Lactobacillus leichmannii.

Abstract

The synthesis of vitamin B12 in four steps from an artificial green secocorrinoid is presented. The stereospecific
reconstitution of the B-ring of the cobalamin involves a quantitative and rapid ligand-centered radical ring closure reaction leading first to a new B12 derivative with antivitamin activity that is subsequently converted to the natural product. Chemoselectivity in the one-electron reduction of the macrocycle was achieved by introducing inorganic cyanide as an axially coordinating protecting group of the otherwise reduction-sensitive Co(III)-ion. The integrity of structure and function of the reconstituted natural product was unequivocally proven by single crystal structural analysis and a microbiological assay using Lactobacillus leichmannii.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:11 October 2016
Deposited On:31 Jan 2017 15:52
Last Modified:05 Feb 2017 06:01
Publisher:American Chemical Society (ACS)
ISSN:1523-7052
Publisher DOI:https://doi.org/10.1021/acs.orglett.6b02611
PubMed ID:27726382

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