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Chemical Compound Review

CHEBI:36110     piperidine-2-carboxylate

Synonyms: AC1NUU41, A825707, 2-Piperidinecarboxylate
This record was replaced with 849.
 
 
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Disease relevance of pipecolate

  • The distinctive astrocytic storage phenomenon and the liver changes are compared to the findings in Zellweger's syndrome and lysinuric protein intolerance, which are also associated with altered pipecolate metabolism [1].
  • The pipecolate-incorporating enzyme for the biosynthesis of the immunosuppressant rapamycin--nucleotide sequence analysis, disruption and heterologous expression of rapP from Streptomyces hygroscopicus [2].
 

High impact information on pipecolate

  • Elucidating the substrate specificity and condensation domain activity of FkbP, the FK520 pipecolate-incorporating enzyme [3].
  • A pipecolate-dependent decarboxylation of [1-14C]malonate was demonstrated in cell-free extracts of R. leguminicola [4].
  • The absence of the gene encoding lysine cyclodeaminase in the sequenced gene cluster and the rest of the genome of NRRL 30748 indicated the synthesis of pipecolate in this strain is not through the common lysine cyclodeamination route previously described for rapamycin and FK506/FK520 biosynthesis [5].
  • [structure: see text] 2-Aryl-2,2-difluoroacetamido-proline and pipecolate esters are high affinity FKBP12 ligands whose rotamase inhibitory activity is comparable to that seen for the corresponding ketoamides [6].
  • A third gene, fkbL, lies at one end of the cluster and encodes lysine cyclodeaminase which catalyzes alpha-deamination and cyclization of the lysine into pipecolate [7].
 

Biological context of pipecolate

 

Anatomical context of pipecolate

  • The metabolic pathways in which peroxisomes are involved include the biosynthesis of ether phospholipids and bile acids, the oxidation of very long chain fatty acids, prostaglandins and unsaturated long chain fatty acids and the catabolism of phytanate and (in man) pipecolate and glyoxylate [9].
 

Associations of pipecolate with other chemical compounds

  • In the presence of added proline derivatives, rapL mutants synthesized novel rapamycin analogs, indicating a relaxed substrate specificity for the enzyme catalyzing pipecolate incorporation into the macrocycle [10].
 

Gene context of pipecolate

 

Analytical, diagnostic and therapeutic context of pipecolate

References

  1. Pathologic alterations in the brain and liver in hyperpipecolic acidemia. Challa, V.R., Geisinger, K.R., Burton, B.K. J. Neuropathol. Exp. Neurol. (1983) [Pubmed]
  2. The pipecolate-incorporating enzyme for the biosynthesis of the immunosuppressant rapamycin--nucleotide sequence analysis, disruption and heterologous expression of rapP from Streptomyces hygroscopicus. König, A., Schwecke, T., Molnar, I., Böhm, G.A., Lowden, P.A., Staunton, J., Leadlay, P.F. Eur. J. Biochem. (1997) [Pubmed]
  3. Elucidating the substrate specificity and condensation domain activity of FkbP, the FK520 pipecolate-incorporating enzyme. Gatto, G.J., McLoughlin, S.M., Kelleher, N.L., Walsh, C.T. Biochemistry (2005) [Pubmed]
  4. Biosynthesis of slaframine, (1S,6S,8aS)-1-acetoxy-6-aminooctahydroindolizine, a parasympathomimetic alkaloid of fungal origin. 3. Origin of the pyrrolidine ring. Clevenstine, E.C., Broquist, H.P., Harris, T.M. Biochemistry (1979) [Pubmed]
  5. Isolation and characterization of meridamycin biosynthetic gene cluster from Streptomyces sp. NRRL 30748. He, M., Haltli, B., Summers, M., Feng, X., Hucul, J. Gene (2006) [Pubmed]
  6. 2-Aryl-2,2-difluoroacetamide FKBP12 ligands: synthesis and X-ray structural studies. Dubowchik, G.M., Vrudhula, V.M., Dasgupta, B., Ditta, J., Chen, T., Sheriff, S., Sipman, K., Witmer, M., Tredup, J., Vyas, D.M., Verdoorn, T.A., Bollini, S., Vinitsky, A. Org. Lett. (2001) [Pubmed]
  7. The biosynthetic gene cluster for the macrolactone ring of the immunosuppressant FK506. Motamedi, H., Shafiee, A. Eur. J. Biochem. (1998) [Pubmed]
  8. The OCT plasmid encodes D-lysine membrane transport and catabolic enzymes in Pseudomonas putida. Cao, X., Kolonay, J., Saxton, K.A., Hartline, R.A. Plasmid (1993) [Pubmed]
  9. Peroxisomal disorders in neurology. Wanders, R.J., Heymans, H.S., Schutgens, R.B., Barth, P.G., van den Bosch, H., Tager, J.M. J. Neurol. Sci. (1988) [Pubmed]
  10. Mutational biosynthesis of novel rapamycins by a strain of Streptomyces hygroscopicus NRRL 5491 disrupted in rapL, encoding a putative lysine cyclodeaminase. Khaw, L.E., Böhm, G.A., Metcalfe, S., Staunton, J., Leadlay, P.F. J. Bacteriol. (1998) [Pubmed]
  11. Synthesis and biological activity of selective pipecolic acid-based TNF-alpha converting enzyme (TACE) inhibitors. Letavic, M.A., Axt, M.Z., Barberia, J.T., Carty, T.J., Danley, D.E., Geoghegan, K.F., Halim, N.S., Hoth, L.R., Kamath, A.V., Laird, E.R., Lopresti-Morrow, L.L., McClure, K.F., Mitchell, P.G., Natarajan, V., Noe, M.C., Pandit, J., Reeves, L., Schulte, G.K., Snow, S.L., Sweeney, F.J., Tan, D.H., Yu, C.H. Bioorg. Med. Chem. Lett. (2002) [Pubmed]
  12. Pipecolic acid is an osmoprotectant for Escherichia coli taken up by the general osmoporters ProU and ProP. Gouesbet, G., Jebbar, M., Talibart, R., Bernard, T., Blanco, C. Microbiology (Reading, Engl.) (1994) [Pubmed]
  13. Modeling the interaction between FK506 and FKBP12: a mechanism for formation of the calcineurin inhibitory complex. Ivery, M.T., Weiler, L. Bioorg. Med. Chem. (1997) [Pubmed]
  14. Biosynthesis of the immunosuppressant immunomycin: the enzymology of pipecolate incorporation. Nielsen, J.B., Hsu, M.J., Byrne, K.M., Kaplan, L. Biochemistry (1991) [Pubmed]
 
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