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Sigma-Aldrich

L-2,4-Diaminobutyric acid dihydrochloride

≥95.0%

Synonym(s):

(2S)-2,4-Diaminobutanoic acid dihydrochloride, L-2,4-Diaminobutanoic acid dihydrochloride

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About This Item

Linear Formula:
NH2CH2CH2CH(NH2)COOH · 2HCl
CAS Number:
1883-09-6
Molecular Weight:
191.06
Beilstein/REAXYS Number:
5763078
EC Number:
217-542-0
MDL number:
MFCD00064561
UNSPSC Code:
12352106
PubChem Substance ID:
329754346
NACRES:
NA.22

Quality Level

100

assay

≥95.0% (AT)
≥95.0%

optical activity

[α]20/D +14.5±1.5°, c = 3.67% in H2O

reaction suitability

reaction type: solution phase peptide synthesis

mp

197-200 °C (dec.)

solubility

water: soluble 0.5 g/10 mL

application(s)

peptide synthesis

SMILES string

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

InChI

1S/C4H10N2O2.2ClH/c5-2-1-3(6)4(7)8;;/h3H,1-2,5-6H2,(H,7,8);2*1H/t3-;;/m0../s1

InChI key

CKAAWCHIBBNLOJ-QTNFYWBSSA-N

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General description

L-2,4-Diaminobutyric acid dihydrochloride is an unnatural amino acid derivative.

Application

L-2,4-Diaminobutyric acid dihydrochloride is suitable reagent used for the differentiation of β-N-methylamino-L-alanine from the diamino acids by using HPLC-FD, UHPLC-UV, UHPLC-MS, and triple quadrupole tandem mass spectrometry (UHPLC-MS/MS). It is suitable reagent used in the quantification of neurotoxin β-N-methylamino-L-alanine (BMAA) in seafood. It may be used as Internal standard for amino acid analysis

Caution

may give off HCl

pictograms

CorrosionExclamation mark
GHS05,GHS07

signalword

Danger

Hazard Classifications

Eye Dam. 1 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

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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Liying Jiang et al.
Scientific reports, 4, 6931-6931 (2014-11-07)
The neurotoxin β-N-methylamino-L-alanine (BMAA) produced naturally by cyanobacteria, diatoms and dinoflagellates can be transferred and accumulated up the food chain, and may be a risk factor for neurodegenerative diseases. This study provides the first systematic screening of BMAA exposure of
Discovery of α,β- and α,γ-diamino acid scaffolds for the inhibition of M1 family aminopeptidases.
Rajesh Gumpena et al.
ChemMedChem, 6(11), 1971-1976 (2011-10-26)
Thomas Krüger et al.
Toxicon : official journal of the International Society on Toxinology, 55(2-3), 547-557 (2009-10-15)
Since diverse taxa of cyanobacteria has been linked to biosynthesis of BMAA, a controversy has arisen about the detection of neurotoxic amino acids in cyanobacteria. In this context, a novel LC-MS/MS method was developed for the unambiguous determination of beta-N-methylamino-L-alanine
Maria Hoernke et al.
Biochimica et biophysica acta, 1818(7), 1663-1672 (2012-03-22)
Basic amino acids play a key role in the binding of membrane associated proteins to negatively charged membranes. However, side chains of basic amino acids like lysine do not only provide a positive charge, but also a flexible hydrocarbon spacer
S A Banack et al.
Toxicon : official journal of the International Society on Toxinology, 56(6), 868-879 (2010-06-22)
The cyanobacterial neurotoxin beta-N-methylamino-L-alanine (BMAA) has been associated with certain forms of progressive neurodegenerative disease, including sporadic Amyotrophic Lateral Sclerosis and Alzheimer's disease. Reports of BMAA in cyanobacterial blooms from lakes, reservoirs, and other water resources continue to be made
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