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Structures of the b- and d-acid derivatives of vitamin B-12 and their complexes with M(CO)(3)](+) (M=Tc-99m, Re)


Spingler, Bernhard; Mundwiler, Stefan; Ruiz-Sanchez, Pilar; van Staveren, Dave R; Alberto, Roger (2007). Structures of the b- and d-acid derivatives of vitamin B-12 and their complexes with M(CO)(3)](+) (M=Tc-99m, Re). European Journal of Inorganic Chemistry, (18):2641-2647.

Abstract

The acid hydrolysis of natural vitamin B-12 yields several products in which the acetamide or propionamide side chains on the corrin framework are converted into the corresponding acids. These acids can be derivatised with further functionalities. We have separated in particular the b- and the d-acid derivatives 1 and 2, respectively, since functionalisation at these positions of the corrin ring generally keeps the affinity for vitamin B-12 transport proteins intact. Although the authenticity of I and 2 seemed evident from 1H NMR investigations, it has not been supported by X-ray structure analysis. The coupling of ethyl N-(3-aminopropyl)-N-(pyridin-2-ylmethyl)glycinate (3) to the carboxylate groups in 1 and 2 by peptide synthetic methods gave the vitamin B-12 derivatives 4 and 5, respectively. The structures of 4 and 5 could be characterised by X-ray analysis, which unambiguously confirmed the presence of the b- and d-acid in 1 and 2, respectively. The reaction of 4 and 5 with the complex Re(OH2)(3)(CO)(3)](+) in water gave the corresponding vitamin B12 derivatives 8 and 9, and the aqueous reaction of 4 and 5 with the complex Tc-99m(OH2)(3)(CO)(3)](+) afforded the Tc-99m homologues 10 and 11, respectively. (C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

Abstract

The acid hydrolysis of natural vitamin B-12 yields several products in which the acetamide or propionamide side chains on the corrin framework are converted into the corresponding acids. These acids can be derivatised with further functionalities. We have separated in particular the b- and the d-acid derivatives 1 and 2, respectively, since functionalisation at these positions of the corrin ring generally keeps the affinity for vitamin B-12 transport proteins intact. Although the authenticity of I and 2 seemed evident from 1H NMR investigations, it has not been supported by X-ray structure analysis. The coupling of ethyl N-(3-aminopropyl)-N-(pyridin-2-ylmethyl)glycinate (3) to the carboxylate groups in 1 and 2 by peptide synthetic methods gave the vitamin B-12 derivatives 4 and 5, respectively. The structures of 4 and 5 could be characterised by X-ray analysis, which unambiguously confirmed the presence of the b- and d-acid in 1 and 2, respectively. The reaction of 4 and 5 with the complex Re(OH2)(3)(CO)(3)](+) in water gave the corresponding vitamin B12 derivatives 8 and 9, and the aqueous reaction of 4 and 5 with the complex Tc-99m(OH2)(3)(CO)(3)](+) afforded the Tc-99m homologues 10 and 11, respectively. (C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

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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:June 2007
Deposited On:23 Oct 2012 12:25
Last Modified:07 Dec 2017 15:40
Publisher:Wiley-Blackwell
ISSN:1434-1948
Publisher DOI:https://doi.org/10.1002/ejic.200601195
Other Identification Number:ISI:000247937300015

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