2,3-Diaminopropionic acid

l-2,3-Diaminopropanoic acid
Names
IUPAC name
3-Amino-L-alanine
Systematic IUPAC name
(2S)-2,3-Diaminopropanoic acid
Identifiers
CAS Number
  • 4033-39-0
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:16303
ChemSpider
  • 87849
KEGG
  • C03401
PubChem CID
  • 97328
UNII
  • JE1TUV83JA
CompTox Dashboard (EPA)
  • DTXSID80193328 Edit this at Wikidata
InChI
  • InChI=1S/C3H8N2O2/c4-1-2(5)3(6)7/h2H,1,4-5H2,(H,6,7)/t2-/m0/s1
    Key: PECYZEOJVXMISF-REOHCLBHSA-N
  • C([C@@H](C(=O)O)N)N
Properties
Chemical formula
 C3H8N2O2
Molar mass 104.109 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Chemical compound

2,3-Diaminopropionic acid (2,3-diaminopropionate, Dpr)[1] is a non-proteinogenic amino acid found in certain secondary metabolites, including zwittermicin A[2] and tuberactinomycin.[3]

Biosynthesis

2,3-Diaminopropionate is formed by the pyridoxal phosphate (PLP) mediated amination of serine.

Biosynthesis of l-2,3 Diaminopropionate

References

  1. ^ Frenkel-Pinter M, Haynes JW, C M, Petrov AS, Burcar BT, Krishnamurthy R, et al. (August 2019). "Selective incorporation of proteinaceous over nonproteinaceous cationic amino acids in model prebiotic oligomerization reactions". Proceedings of the National Academy of Sciences of the United States of America. 116 (33): 16338–16346. doi:10.1073/pnas.1904849116. PMC 6697887. PMID 31358633.
  2. ^ Rogers EW, Molinski TF (February 2007). "Asymmetric synthesis of diastereomeric diaminoheptanetetraols. A proposal for the configuration of (+)-zwittermicin a". Organic Letters. 9 (3): 437–40. doi:10.1021/ol062804a. PMC 2729442. PMID 17249781.
  3. ^ Thomas MG, Chan YA, Ozanick SG (September 2003). "Deciphering tuberactinomycin biosynthesis: isolation, sequencing, and annotation of the viomycin biosynthetic gene cluster". Antimicrobial Agents and Chemotherapy. 47 (9): 2823–30. doi:10.1128/AAC.47.9.2823-2830.2003. PMC 182626. PMID 12936980.