:2,3-Diaminopropionic acid

{{Chembox

| Name ={{sm|l}}-2,3-Diaminopropanoic acid

| ImageFile = L-2,3-Diaminopropanoic acid.svg

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| IUPACName = 3-Amino-L-alanine

| SystematicName = (2S)-2,3-Diaminopropanoic acid

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|Section1={{Chembox Identifiers

| CASNo = 4033-39-0

| PubChem = 97328

| ChemSpiderID = 87849

| ChEBI = 16303

| KEGG = C03401

| UNII = JE1TUV83JA

| SMILES = C([C@@H](C(=O)O)N)N

| StdInChI = 1S/C3H8N2O2/c4-1-2(5)3(6)7/h2H,1,4-5H2,(H,6,7)/t2-/m0/s1

| StdInChIKey = PECYZEOJVXMISF-REOHCLBHSA-N

}}

|Section2={{Chembox Properties

| C=3 | H=8 | N=2 | O=2

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|Section3={{Chembox Hazards

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{{Distinguish|Diaminopimelic acid}}

2,3-Diaminopropionic acid (2,3-diaminopropionate, Dpr){{cite journal | vauthors = Frenkel-Pinter M, Haynes JW, C M, Petrov AS, Burcar BT, Krishnamurthy R, Hud NV, Leman LJ, Williams LD | display-authors = 6 | title = Selective incorporation of proteinaceous over nonproteinaceous cationic amino acids in model prebiotic oligomerization reactions | journal = Proceedings of the National Academy of Sciences of the United States of America | volume = 116 | issue = 33 | pages = 16338–16346 | date = August 2019 | pmid = 31358633 | pmc = 6697887 | doi = 10.1073/pnas.1904849116 | doi-access = free }} is a non-proteinogenic amino acid found in certain secondary metabolites, including zwittermicin A{{cite journal | vauthors = Rogers EW, Molinski TF | title = Asymmetric synthesis of diastereomeric diaminoheptanetetraols. A proposal for the configuration of (+)-zwittermicin a | journal = Organic Letters | volume = 9 | issue = 3 | pages = 437–40 | date = February 2007 | pmid = 17249781 | pmc = 2729442 | doi = 10.1021/ol062804a }} and tuberactinomycin.{{cite journal | vauthors = Thomas MG, Chan YA, Ozanick SG | title = Deciphering tuberactinomycin biosynthesis: isolation, sequencing, and annotation of the viomycin biosynthetic gene cluster | journal = Antimicrobial Agents and Chemotherapy | volume = 47 | issue = 9 | pages = 2823–30 | date = September 2003 | pmid = 12936980 | pmc = 182626 | doi = 10.1128/AAC.47.9.2823-2830.2003 }}

Biosynthesis

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

Image:Diaminosynthesis.png{{clear-left}}

References

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{{DEFAULTSORT:Diaminopropionate, 2,3-}}

Category:2,3-Diaminopropionic acids