Alpha-ketoacid

Mac, M. and Nalecz, K. A. Expression of monocarboxylic acid transporters (MCT) in brain cells. Implication for branched chain alpha-ketoacids transport in neurons. Neurochem. Int. 43 305-309, 2003. 

Burka LT, Doran J, Wilson BJ. Enzyme inhibition and the toxic action of moniliformin and other vinylogous alpha-ketoacids. Biochem. Pharmacol. 1982 31 79-84. 

Wynn RM, Davie JR, Chuang JL, Cote CD, Chuang DT. Impaired assembly of El decarboxylase of the branched-chain alpha-ketoacid dehydrogenase complex in type lA maple syrup urine disease. J Biol Chem 1998 273 13110-8. 

J. D. Rozzell, Alpha Amino Acids from Alpha Ketoacids Using Coupled Transaminase Enzymes, 1989, U. S. Patent 4,518,692. 

Lipoamide reductase (NADH). E3 component of alpha-ketoacid dehydrogenase complexes. Lipoyl dehydrogenase. Dihydrolipoyl dehydrogenase. 

Alpha-carboxylase. Pyruvic decarboxylase. Alpha-ketoacid carboxylase. 

Recent studies with bovine heart mitochondrial matrix preparations indicate that one of the major products of this pathway is octanoyl-ACP and these newly synthesized octanoyl moieties can be translocated directly to the lipoylation site of the glycine cleavage apo-H protein (S. Smith, 2007). Octanoylated mitochondrial proteins are the substrates for the enzyme lipoic acid synthase, which inserts two sulfur atoms at the C6 and C8 positions of the octanoyl moiety. These results are consistent with the hypothesis that one of the major roles of the mitochondrial FAS pathway in all eukaryotes is to ensure that an adequate supply of lipoyl moieties is always available to service the glycine cleavage enzyme and the alpha-ketoacid dehydrogenases that are essential to mitochondrial function. 

Blaser, H.U. and Jalett, H.-P. (1993) Enantioselective hydrogenation of alpha-ketoacids using Pt-catalysts modified with cinchona alkaloids. Stud. 

Scheme 9 Formation of alpha-ketoacids by oxidation of phosphorous and sulfur ylides. This wOTk was inspired by sulfur yfide chemistry used in oin synthesis of bullvafene...

Ju L, Bode JW (2010) Amide formation by decarboxylative condensation of hydroxylamines and alpha-ketoacids synthesis of N-[(lS)-l-phenylethyl]-benzeneacetamide. Organic Synth 87 218-225... 

Ju L, Bode JW (2009) A general strategy for the preparation of C-terminal peptide alpha-ketoacids by solid phase peptide synthesis. Org Biomol Chem 7 2259-2264... 

Flores MA, Bode JW (2010) Chemoselective protection of alpha-ketoacids by direct annulations with oximes. Org Lett 12 1924-1927... 

Fuknzumi T, Ju L, Bode JW (2012) Chemoselective cyclization of improtected linear peptides by alpha-ketoacid-hydroxylamine amide-ligation. Org Biomol Chem 10 5837-5844... 

PLP is the coenzyme of more than 160 enzymes catalyzing a broad variety of reactions, predominantly involving an amino acid, an amine, or an oxoacid. Some of the selective examples are (1) the transfer of the alpha amine group from an amino acid to a ketoacid, catalyzed by transaminases, (2) the elimination or replacement of the substituent in the beta position of an amino acid or other compounds, catalyzed by lyases and synthases, respectively, and (3) the removal of the alpha carboxylic group from amino acids or other compounds, catalyzed by decarboxylases. More complex reactions are also carried out, involving, for example. 

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