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Functionalization of glucose at position C-3 for transition metal coordination: Organo-rhenium complexes with carbohydrate skeletons


Dumas, C; Petrig, J; Frei, L; Spingler, Bernhard; Schibli, R (2005). Functionalization of glucose at position C-3 for transition metal coordination: Organo-rhenium complexes with carbohydrate skeletons. Bioconjugate Chemistry, 16(2):421-428.

Abstract

Novel 3-O-1,2;5,6-di-O-isopropylidene-alpha-D-glueofuranose] and 3-O-D-glucose] derivatives with an iminodiacetate (N,O,O), a histidinate, and an N-(acetetyl)picolylamine (N,N,O) chelating system for tridentate coordination of the organometallic M(CO)(3)-fragment (M = Tc, Re) have been prepared. The chelates were introduced and assembled through reductive amination starting from 3-O-1,2;5,6-di-O-isopropylidene-alpha-D-glucofuranose]-acetaldehyde. After deprotection, the pyranose derivatives were reacted with the precursor NEt4](2)ReBr3(CO)(3)] to afford the corresponding organometallic complexes in yields between 54% and 94%. The NMR, MS, and IR analyses corroborated the tridentate coordination of the organometallic metal center exclusively via the synthetic chelates. In the case of the N-(acetyl)picolylamine derivative, the coordinative properties were further confirmed by X-ray structure analysis of the first Re(CO)(3)-D-glucofuranose complex. All glucose complexes unveiled good stability and solubility in organic and aqueous media.

Abstract

Novel 3-O-1,2;5,6-di-O-isopropylidene-alpha-D-glueofuranose] and 3-O-D-glucose] derivatives with an iminodiacetate (N,O,O), a histidinate, and an N-(acetetyl)picolylamine (N,N,O) chelating system for tridentate coordination of the organometallic M(CO)(3)-fragment (M = Tc, Re) have been prepared. The chelates were introduced and assembled through reductive amination starting from 3-O-1,2;5,6-di-O-isopropylidene-alpha-D-glucofuranose]-acetaldehyde. After deprotection, the pyranose derivatives were reacted with the precursor NEt4](2)ReBr3(CO)(3)] to afford the corresponding organometallic complexes in yields between 54% and 94%. The NMR, MS, and IR analyses corroborated the tridentate coordination of the organometallic metal center exclusively via the synthetic chelates. In the case of the N-(acetyl)picolylamine derivative, the coordinative properties were further confirmed by X-ray structure analysis of the first Re(CO)(3)-D-glucofuranose complex. All glucose complexes unveiled good stability and solubility in organic and aqueous media.

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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:March 2005
Deposited On:23 Oct 2012 14:02
Last Modified:05 Apr 2016 16:01
Publisher:American Chemical Society
ISSN:1043-1802
Publisher DOI:https://doi.org/10.1021/bc049744i
Other Identification Number:ISI:000227732300023

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