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33270

Sigma-Aldrich

L-2,3-Diaminopropionic acid hydrochloride

≥97.0%

Synonym(s):

3-Amino-L-alanine hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C3H8N2O2 · HCl
CAS Number:
1482-97-9
Molecular Weight:
140.57
Beilstein:
4263944
MDL number:
MFCD00065497
UNSPSC Code:
12352202
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[1]

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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)
Yohan Park et al.
Organic letters, 11(16), 3738-3741 (2009-07-29)
An efficient enantioselective synthetic method for (S)-alpha-alkyl-alpha,beta-diaminopropionic acid is reported. The asymmetric phase-transfer catalytic alkylation of N(1)-Boc-2-phenyl-2-imidazoline-4-carboxylic acid tert -butyl ester in the presence of chiral quaternary ammonium catalyst gave the corresponding alkylated products (93-98% ee) which could be transformed
Huan-Huan Zhang et al.
The Journal of organic chemistry, 73(9), 3634-3637 (2008-03-28)
A novel and convenient route to the asymmetric synthesis of 2,3-diamino acids via Mannich reaction of iminolactones 1a and 1b with N-protected imines has been achieved in good yields (up to 95%) and high diastereoselectivity (dr: >99:1). Hydrolysis of the
Yun Lan et al.
Chembiochem : a European journal of chemical biology, 11(9), 1266-1272 (2010-05-19)
Nonviral vectors that harness the change in pH in endosomes, are increasingly being used to deliver cargoes, including nucleic acids, into mammalian cells. Here we present evidence that the pK(a) of the beta-NH(2) in 2,3-diaminopropionic acid (Dap) is sufficiently lowered
James E Beddow et al.
Organic & biomolecular chemistry, 5(17), 2812-2825 (2007-08-19)
Conjugate addition of lithium dibenzylamide to (S)-N(3)-acryloyl-4-isopropyl-5,5-dimethyloxazolidin-2-one (derived from l-valine) and alkylation of the resultant lithium beta-amino enolate provides, after deprotection, a range of (S)-2-alkyl-3-aminopropanoic acids in good yield and high ee. Alternatively, via a complementary pathway, conjugate addition of
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