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<ref>{{cite journal | vauthors = Mothet JP, Parent AT, Wolosker H, Brady RO, Linden DJ, Ferris CD, Rogawski MA, Snyder SH | title = D-serine is an endogenous ligand for the glycine site of the N-methyl-D-aspartate receptor.| journal = Proceedings of the National Academy of Sciences of the United States of America | volume = 97 | issue = 9 | pages = 4926–31 | date = Apr 2000 | pmid = 10781100 | pmc = 18334 | doi = 10.1073/pnas.97.9.4926 | bibcode = 2000PNAS...97.4926M }}</ref> <ref>{{cite journal | vauthors = Mothet JP, Parent AT, Wolosker H, Brady RO, Linden DJ, Ferris CD, Rogawski MA, Snyder SH | title = D-serine is an endogenous ligand for the glycine site of the N-methyl-D-aspartate receptor.| journal = Proceedings of the National Academy of Sciences of the United States of America | volume = 97 | issue = 9 | pages = 4926–31 | date = Apr 2000 | pmid = 10781100 | pmc = 18334 | doi = 10.1073/pnas.97.9.4926 | bibcode = 2000PNAS...97.4926M }}</ref>


Bacteria:
The major sources of D-amino acids in Nature are ]. In these microorganisms, D-amino acids are part of ] (a major component of the bacterial cell wall). In addition, also the compounds ] and ] contain D-amino acids. The major sources of D-amino acids in Nature are ]. In these microorganisms, D-amino acids are part of ] (a major component of the bacterial cell wall). In addition, also the compounds ] and ] contain D-amino acids.



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The chiral forms of serine. Left: L-enantiomer, right: D-enantiomer

Amino acids are chiral compounds that are present in living organisms as free compounds or as polymers such as peptides or proteins. The 20 L-Amino acids present in proteins and peptides are defined as proteinogenic amino acid. About 500 amino acids are known and have been classified in many ways base on their chemical/physical properties.

All α-amino acids (AA) but glycine exist in either of the two enantiomers, which are mirror images of each other (the so called D- and L-enantiomers).

Although present in a less concentration in mammals, free D-amino acids play central roles: as an example D-serine is one of the main neuromodulators of the glutamatergic neurotransmission and D-aspartate is fundamental for brain development in fetus.

The major sources of D-amino acids in Nature are bacteria. In these microorganisms, D-amino acids are part of peptidoglycan (a major component of the bacterial cell wall). In addition, also the compounds teichoic acids and poly-γ-glutamate contain D-amino acids.

In peptidoglycan, D-alanine or D-glutamate contribute to antibiotic resistance in some bacteria. Many diverse bacteria synthesize D-amino acids such as, D-methionine and D-leucine.

D-amino acids are also present in many venoms from platypus, funnel web spider, and cone snail produced by the action of isomerases.

References

  1. Wagner I, Musso H (November 1983). "New Naturally Occurring Amino Acids". Angewandte Chemie International Edition in English. 22 (11): 816–28. doi:10.1002/anie.198308161.Closed access icon
  2. Katane M, Homma H (June 2010). "D-aspartate oxidase: the sole catabolic enzyme acting on free D-aspartate in mammals". Chem Biodivers. 7 (6): 1435–49. doi:10.1002/cbdv.200900250. PMID 20564562.
  3. Mothet JP, Parent AT, Wolosker H, Brady RO, Linden DJ, Ferris CD, Rogawski MA, Snyder SH (April 2000). "D-serine is an endogenous ligand for the glycine site of the N-methyl-D-aspartate receptor". Proceedings of the National Academy of Sciences of the United States of America. 97 (9): 4926–31. Bibcode:2000PNAS...97.4926M. doi:10.1073/pnas.97.9.4926. PMC 18334. PMID 10781100.
  4. Radkov AD, Moe LA (2014). "Bacterial synthesis of D-amino acids". Appl Microbiol Biotechnol. 98: 5363–74. doi:10.1007/s00253-014-5726-3.

External links

Encoded (proteinogenic) amino acids
General topics
Unspecified L-amino acid
By properties
Aliphatic
Aromatic
Polar, uncharged
Positive charge (pKa)
Negative charge (pKa)
Protein primary structure and posttranslational modifications
General
N terminus
C terminus
Single specific AAs
Serine/Threonine
Tyrosine
Cysteine
Aspartate
Glutamate
Asparagine
Glutamine
Lysine
Arginine
Proline
Histidine
Tryptophan
Crosslinks between two AAs
CysteineCysteine
MethionineHydroxylysine
LysineTyrosine
TryptophanTryptophan
Crosslinks between three AAs
SerineTyrosineGlycine
HistidineTyrosineGlycine
AlanineSerineGlycine
Crosslinks between four AAs
AllysineAllysineAllysineLysine
Metabolism: Protein metabolism, synthesis and catabolism enzymes
Essential amino acids are in Capitals
Kacetyl-CoA
LYSINE
LEUCINE

(See Template:Leucine metabolism in humans – this diagram does not include the pathway for β-leucine synthesis via leucine 2,3-aminomutase)

TRYPTOPHAN
PHENYLALANINEtyrosine
  • (see below)
G
G→pyruvate
citrate
glycineserine
alanine
cysteine
threonine
G→glutamate
α-ketoglutarate
HISTIDINE
proline
arginine
alpha-ketoglutarate→TCA
Other
G→propionyl-CoA
succinyl-CoA
VALINE
ISOLEUCINE
METHIONINE
THREONINE
succinyl-CoA→TCA
G→fumarate
PHENYLALANINEtyrosine
G→oxaloacetate
asparagineaspartate
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