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MetaCyc Pathway: lysine degradation VI

Enzyme View:

This view shows enzymes only for those organisms listed below, in the list of taxa known to possess the pathway. If an enzyme name is shown in bold, there is experimental evidence for this enzymatic activity.

Superclasses: Degradation/Utilization/Assimilation Amino Acids Degradation Lysine Degradation

Some taxa known to possess this pathway include ? : Streptomyces clavuligerus , [Flavobacterium] lutescens

Expected Taxonomic Range: Actinobacteria , Proteobacteria

Summary:
Several different enzymes convert L-lysine to (S)-2-amino-6-oxohexanoate, as shown in MetaCyc pathways lysine degradation VI, lysine degradation VIII and lysine degradation IX.

In this pathway, L-lysine is converted to (S)-2-amino-6-oxohexanoate by L-lysine 6-aminotransferase. (S)-2-amino-6-oxohexanoate is subsequently cyclized by spontaneous intramolecular dehydration to (S)-2,3,4,5-tetrahydropiperidine-2-carboxylate [Soda68, Tanizawa85, Fujii00a].

This enzymatic activity has been shown in the γ-proteobacterium Flavobacterium lutescens IFO3084 (previously known as Achromobacter liquidum) [Tanizawa85] and in the actinomycete Streptomyces clavuligerus.

Further catabolism of L-2-aminoadipate in [Flavobacterium] lutescens has not been described although in some other γ-proteobacteria it is catabolized to glutarate (see MetaCyc pathway lysine degradation V).

Iin Streptomyces clavuligerus L-2-aminoadipate is a precursor of β-lactam antibiotics and is a substrate for δ-(L-α-aminoadipyl)-L-cysteinyl-D-valine synthetase (see isopenicillin N biosynthesis) [deLa97].

Superpathways: superpathway of lysine degradation

Variants: lysine degradation I , lysine degradation II (mammalian) , lysine degradation II (pipecolate pathway) , lysine degradation III , lysine degradation IV , lysine degradation V , lysine degradation VII , lysine degradation VIII , lysine degradation IX , lysine degradation X , lysine fermentation to acetate and butyrate

Credits:
Created 28-Aug-2006 by Fulcher CA , SRI International
Revised 08-Sep-2009 by Caspi R , SRI International


References

deLa97: de La Fuente JL, Rumbero A, Martin JF, Liras P (1997). "Delta-1-piperideine-6-carboxylate dehydrogenase, a new enzyme that forms alpha-aminoadipate in Streptomyces clavuligerus and other cephamycin C-producing actinomycetes." Biochem J 327 ( Pt 1);59-64. PMID: 9355735

Fujii00: Fujii T, Narita T, Agematu H, Agata N, Isshiki K (2000). "Cloning and characterization of pcd encoding delta'-piperideine-6-carboxylate dehydrogenase from flavobacterium lutescens IFO3084." J Biochem (Tokyo) 128(6);975-82. PMID: 11098140

Fujii00a: Fujii T, Narita T, Agematu H, Agata N, Isshiki K (2000). "Characterization of L-lysine 6-aminotransferase and its structural gene from Flavobacterium lutescens IFO3084." J Biochem (Tokyo) 128(3);391-7. PMID: 10965037

Soda68: Soda K, Misono H, Yamamoto T (1968). "L-Lysine:alpha-ketoglutarate aminotransferase. I. Identification of a product, delta-1-piperideine-6-carboxylic acid." Biochemistry 7(11);4102-9. PMID: 5722275

Tanizawa85: Tanizawa K, Yoshimura T, Soda K (1985). "L-Lysine transaminase from Flavobacterium lutescens." Methods Enzymol 113;96-102. PMID: 4088080

Zabriskie00: Zabriskie TM, Jackson MD (2000). "Lysine biosynthesis and metabolism in fungi." Nat Prod Rep 17(1);85-97. PMID: 10714900

Other References Related to Enzymes, Genes, Subpathways, and Substrates of this Pathway

Calvert66: Calvert AF, Rodwell VW (1966). "Metabolism of pipecolic acid in a Pseudomonas species. 3. L-alpha-aminoadipate delta-semialdehyde:nicotinamide adenine dinucleotide oxidoreductase." J Biol Chem 241(2);409-14. PMID: 4285660

Hammer92: Hammer T, Bode R (1992). "Purification and characterization of an inducible L-lysine: 2-oxoglutarate 6-aminotransferase from Candida utilis." J Basic Microbiol 32(1);21-7. PMID: 1527704

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Mills06: Mills PB, Struys E, Jakobs C, Plecko B, Baxter P, Baumgartner M, Willemsen MA, Omran H, Tacke U, Uhlenberg B, Weschke B, Clayton PT (2006). "Mutations in antiquitin in individuals with pyridoxine-dependent seizures." Nat Med 12(3);307-9. PMID: 16491085

PerezLlarena98: Perez-Llarena FJ, Rodriguez-Garcia A, Enguita FJ, Martin JF, Liras P (1998). "The pcd gene encoding piperideine-6-carboxylate dehydrogenase involved in biosynthesis of alpha-aminoadipic acid is located in the cephamycin cluster of Streptomyces clavuligerus." J Bacteriol 180(17);4753-6. PMID: 9721323

Rodwell71: Rodwell V.W. (1971). "Δ1-Piperideine-6-carboxylic acid and α-aminoadipic acid δ-semialdehyde." Methods Enzymol. 178:188-199.

Romero97: Romero J, Martin JF, Liras P, Demain AL, Rius N (1997). "Partial purification, characterization and nitrogen regulation of the lysine epsilon-aminotransferase of Streptomyces clavuligerus." J Ind Microbiol Biotechnol 18(4);241-6. PMID: 9172431

Soda68a: Soda K, Misono H (1968). "L-Lysine:alpha-ketoglutarate aminotransferase. II. Purification, crystallization, and properties." Biochemistry 7(11);4110-9. PMID: 5722276

Tobin91: Tobin MB, Kovacevic S, Madduri K, Hoskins JA, Skatrud PL, Vining LC, Stuttard C, Miller JR (1991). "Localization of the lysine epsilon-aminotransferase (lat) and delta-(L-alpha-aminoadipyl)-L-cysteinyl-D-valine synthetase (pcbAB) genes from Streptomyces clavuligerus and production of lysine epsilon-aminotransferase activity in Escherichia coli." J Bacteriol 173(19);6223-9. PMID: 1917855


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 18.5 on Fri Nov 28, 2014, BIOCYC13A.