Carbon exchange in hot alkaline degradation of glucose

Ellis, A; Wilson, MA

Carbon exchange in hot alkaline degradation of glucose

Ellis, A Wilson, MA

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Publisher:: American Chemical Society
Publication Type:: Journal Article
Citation:: Ellis, A. and Wilson, M. 2002 'Carbon exchange in hot alkaline degradation of glucose', Journal of Organic Chemistry, vol. 67, no. 24, pp. 8469-8474.
Issue Date:: 2002

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Field	Value	Language
dc.contributor.author	Ellis, A	en_US
dc.contributor.author	Wilson, MA	en_US
dc.date.accessioned	2009-06-26T04:10:51Z
dc.date.available	2009-06-26T04:10:51Z
dc.date.issued	2002	en_US
dc.identifier	2004002984	en_US
dc.identifier.citation	Ellis, A. and Wilson, M. 2002 'Carbon exchange in hot alkaline degradation of glucose', Journal of Organic Chemistry, vol. 67, no. 24, pp. 8469-8474.	en_US
dc.identifier.issn	0022-3263	en_US
dc.identifier.other	C1	en_US
dc.identifier.uri	http://hdl.handle.net/10453/557
dc.description.abstract	The decomposition ofl-13C-o-glucose, 6-13C-o-glucose, and 1-13C-sodium lactate has been studied in hot (145 ± 3°C) alkaline (3.5 M) sodium hydroxide solution in order to understand the mechanisms of carbon exchange in the alkaline degradation of glucose. The results show that in the formation oflactate from glucose the carboxylate (COO-) carbon is formed preferentially from Cl carbons but methyl (ClIa) carbon is formed preferentially from C6 carbons. However, on further decomposition of lactate to ethanol and carbonate, 13C-Iabeled carboxylate (COO-) is scrambled equally among carbonate and both carbons in product ethanol molecules. In the production of glycolate, the labeled Cl carbon mainly ends up as carboxylate (COO-) carbon, while for C6-labeled glucose the labeled carbon mainly ends up as alcoholic (CH20H) carbon. In the production of acetate and formate there is also discrimination between Cl and C6 label.	en_US
dc.publisher	American Chemical Society	en_US
dc.relation.ispartof	Journal of Organic Chemistry	en_US
dc.relation.isbasedon	http//dx.doi.org/10.1021/jo025912t	en_US
dc.title	Carbon exchange in hot alkaline degradation of glucose	en_US
dc.type	Journal article
utslib.citation.volume	67	en_US
utslib.citation.number	24	en_US
utslib.location	Washington D.C.	en_US
utslib.citation.startpage	8469	en_US
utslib.citation.endpage	8474	en_US
utslib.identifier.org	Science	en_US
utslib.copyright.status	closed_access

Abstract:

The decomposition ofl-13C-o-glucose, 6-13C-o-glucose, and 1-13C-sodium lactate has been studied in hot (145 ± 3°C) alkaline (3.5 M) sodium hydroxide solution in order to understand the mechanisms of carbon exchange in the alkaline degradation of glucose. The results show that in the formation oflactate from glucose the carboxylate (COO-) carbon is formed preferentially from Cl carbons but methyl (ClIa) carbon is formed preferentially from C6 carbons. However, on further decomposition of lactate to ethanol and carbonate, 13C-Iabeled carboxylate (COO-) is scrambled equally among carbonate and both carbons in product ethanol molecules. In the production of glycolate, the labeled Cl carbon mainly ends up as carboxylate (COO-) carbon, while for C6-labeled glucose the labeled carbon mainly ends up as alcoholic (CH20H) carbon. In the production of acetate and formate there is also discrimination between Cl and C6 label.

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