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33270

Sigma-Aldrich

L-2,3-Diaminopropionic acid hydrochloride

≥97.0%

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Synonym(s):
3-Amino-L-alanine hydrochloride
Empirical Formula (Hill Notation):
C3H8N2O2 · HCl
CAS Number:
1482-97-9
Molecular Weight:
140.57
Beilstein:
4263944
MDL number:
MFCD00065497
UNSPSC Code:
12352200
PubChem Substance ID:
329754483

Assay

≥97.0% (AT)
≥97.0%

form

solid

optical activity

[α]20/D +24±2°, c = 2% in 0.5 M HCl

loss

<1% loss on drying

mp

231-233 °C (dec.)

application(s)

peptide synthesis

SMILES string

O=C(O)[C@H](CN)N.Cl

InChI

1S/C3H8N2O2.ClH/c4-1-2(5)3(6)7;/h2H,1,4-5H2,(H,6,7);1H/t2-;/m0./s1

InChI key

SKWCZPYWFRTSDD-DKWTVANSSA-N

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Other Notes

Substrate for (Km =1mM), and competitive inhbitor (Ki =1mM, L-homoserine as substrate) of cystathionase from rat liver

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Rat liver L-diaminopropionate ammonia lyase. Identification as cystathionase.
I K Mushahwar et al.
The Journal of biological chemistry, 248(21), 7407-7411 (1973-11-10)
Giovanni N Roviello et al.
Amino acids, 43(6), 2537-2543 (2012-06-13)
In this work, we report a synthetic approach to a Fmoc-protected nucleoamino acid, based on L-diaminopropanoic acid, carrying the DNA nucleobase on the alpha-amino group by means of an amide bond, suitable for the solid-phase synthesis of novel nucleopeptides of
Joana R Viola et al.
Bioorganic & medicinal chemistry letters, 22(17), 5635-5638 (2012-08-04)
Here we report a novel class of peptides-d-diaminopropionic acids (Dap)-for gene delivery. These peptides have attractive properties for gene delivery, and the advantage that they can be easily manipulated in relation to their composition, abiding with tailored-design. We characterized the
Changming Zhao et al.
FEBS letters, 582(20), 3125-3131 (2008-08-12)
Zwittermicin A (ZwA) is a hybrid polyketide-non-ribosomal peptide that is thought to be biosynthesized from five proposed building blocks, including the 2,3-diaminopropionate. Candidate genes for de novo biosynthesis of 2,3-diaminopropionate, zwa5A and zwa5B, have been identified in a previous study.
Johnson Cheung et al.
Molecular microbiology, 74(3), 594-608 (2009-09-25)
Siderophores are iron-scavenging molecules produced by many microbes. In general, they are synthesized using either non-ribosomal peptide synthetase (NRPS) or NRPS-independent siderophore (NIS) pathways. Staphylococcus aureus produces siderophores, of which the structures of staphyloferrin A and staphyloferrin B are known.
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