From Wikipedia, the free encyclopedia
1-Pyrroline-5-carboxylic acid
Names
Preferred IUPAC name
3,4-Dihydro-2H -pyrrole-2-carboxylic acid
Other names
1-Pyrroline-5-carboxylic acid δ-1-Pyrroline-5-carboxylic acid P5C
Identifiers
ChEBI
ChEMBL
ChemSpider
KEGG
MeSH
Delta-1-pyrroline-5-carboxylate
UNII
InChI=1S/C5H7NO2/c7-5(8)4-2-1-3-6-4/h3-4H,1-2H2,(H,7,8)
Y Key: DWAKNKKXGALPNW-UHFFFAOYSA-N
Y InChI=1/C5H7NO2/c7-5(8)4-2-1-3-6-4/h3-4H,1-2H2,(H,7,8)
Key: DWAKNKKXGALPNW-UHFFFAOYAB
C1CC(N=C1)C(=O)O
O=C(O)C1/N=C\CC1
Properties
C5 H7 NO2
Molar mass
113.115 g/mol
Acidity (pK a )
1.82/6.07
[1]
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
1-Pyrroline-5-carboxylic acid (systematic name 3,4-dihydro-2H-pyrrole-2-carboxylic acid
[2] ) is a cyclic
imino acid . Its
conjugate base and
anion is 1-pyrroline-5-carboxylate (P5C). In solution, P5C is in spontaneous
equilibrium with
glutamate-5-semialdhyde (GSA).
[3]
Biochemistry
The
stereoisomer (S )-1-pyrroline-5-carboxylate (also referred to as L-P5C) is an intermediate
metabolite in the biosynthesis and degradation of
proline and
arginine .
[4]
[5]
[6]
In
prokaryotic proline biosynthesis, GSA is synthesized from
γ-glutamyl phosphate by the enzyme
γ-glutamyl phosphate reductase . In most
eukaryotes , GSA is synthesised from the
amino acid
glutamate by the bifunctional enzyme
1-pyrroline-5-carboxylate synthase (P5CS). The human P5CS is encoded by the
ALDH18A1
gene .
[7]
[8] The
enzyme
pyrroline-5-carboxylate reductase converts P5C into proline.
In proline degradation, the enzyme
proline dehydrogenase produces P5C from proline, and the enzyme
1-pyrroline-5-carboxylate dehydrogenase converts GSA to glutamate. In many prokaryotes, proline dehydrogenase and P5C dehydrogenase form a bifunctional enzyme that prevents the release of P5C during proline degradation.
[9]
References
^
"computed by Chemicalize from ChemAxon" .
^ PubChem.
"3,4-Dihydro-2H-pyrrole-2-carboxylic acid" . pubchem.ncbi.nlm.nih.gov . Retrieved 2020-01-23 .
^ Heacock, Anne M.; Williams, Irene H.; Frank, Leonard H.; Adams, Elijah (1975-04-01). "Δ1-Pyrroline-5-carboxylate and Δ1-pyrroline-3-hydroxy-5-carboxylate: Chromatography on the amino acid analyzer". Analytical Biochemistry . 64 (2): 593–600.
doi :
10.1016/0003-2697(75)90472-8 .
ISSN
0003-2697 .
PMID
236687 .
^ Bertolo, Robert F.; Burrin, Douglas G. (2008-10-01).
"Comparative Aspects of Tissue Glutamine and Proline Metabolism" . The Journal of Nutrition . 138 (10): 2032S–2039S.
doi :
10.1093/jn/138.10.2032S .
ISSN
0022-3166 .
PMID
18806120 .
^ Qamar, Aarzoo; Mysore, Kirankumar; Senthil-Kumar, Muthappa (2015).
"Role of proline and pyrroline-5-carboxylate metabolism in plant defense against invading pathogens" . Frontiers in Plant Science . 6 : 503.
doi :
10.3389/fpls.2015.00503 .
ISSN
1664-462X .
PMC
4491715 .
PMID
26217357 .
^ Winter, Gudrun; Todd, Christopher D.; Trovato, Maurizio; Forlani, Giuseppe; Funck, Dietmar (2015).
"Physiological implications of arginine metabolism in plants" . Frontiers in Plant Science . 6 : 534.
doi :
10.3389/fpls.2015.00534 .
ISSN
1664-462X .
PMC
4520006 .
PMID
26284079 .
^ Liu G, Maunoury C, Kamoun P, Aral B (Oct 1996). "Assignment of the human gene encoding the delta 1-pyrroline-5-carboxylate synthetase (P5CS) to 10q24.3 by in situ hybridization". Genomics . 37 (1): 145–6.
doi :
10.1006/geno.1996.0535 .
PMID
8921385 .
^
"Entrez Gene: ALDH18A1 aldehyde dehydrogenase 18 family, member A1" .
^ Liu, Li-Kai; Becker, Donald F.; Tanner, John J. (2017-10-15).
"Structure, function, and mechanism of proline utilization A (PutA)" . Archives of Biochemistry and Biophysics . Flavoproteins: Beyond the Classical Paradigms. 632 : 142–157.
doi :
10.1016/j.abb.2017.07.005 .
ISSN
0003-9861 .
PMC
5650515 .
PMID
28712849 .