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Sigma-Aldrich

DL-2,3-Diaminopropionic acid monohydrochloride

98%

Synonym(s):

3-Amino-DL-alanine monohydrochloride

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About This Item

Linear Formula:
NH2CH2CH(NH2)COOH · HCl
CAS Number:
54897-59-5
Molecular Weight:
140.57
Beilstein/REAXYS Number:
5293359
EC Number:
259-387-1
MDL number:
MFCD00012884
UNSPSC Code:
12352106
PubChem Substance ID:
24853139
NACRES:
NA.22

assay

98%

form

solid

reaction suitability

reaction type: solution phase peptide synthesis

mp

232 °C (dec.) (lit.)

application(s)

peptide synthesis

SMILES string

Cl[H].NCC(N)C(O)=O

InChI

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

InChI key

SKWCZPYWFRTSDD-UHFFFAOYSA-N

Related Categories

General description

DL-2,3-Diaminopropionic acid monohydrochloride also known as 3-Amino-DL-alanine monohydrochloride, is commonly used in solution phase peptide synthesis.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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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
Kamila Stokowa et al.
Journal of inorganic biochemistry, 106(1), 111-116 (2011-11-25)
Capreomycin is an important therapeutic agent having intriguing and diverse molecular features. Its polypeptidic structure rich in nitrogen donors makes the drug a promising chelating agent for a number of transition metal ions, especially for copper(II). The results of the
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
Min Zhong et al.
Bioorganic & medicinal chemistry letters, 21(1), 307-310 (2010-11-27)
This letter describes the structure-activity relationship (SAR) of the 'right-wing' α-amino acid residue of potent tetrahydroisoquinoline (THIQ)-derived LFA-1/ICAM-1 antagonists. Novel (S)-substituted heteroaryl-bearing α-amino acids have been identified as replacements of the 'right-wing' (S)-2,3-diaminopropanoic acid (DAP) moiety. Improvement of potency in
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
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