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Sigma-Aldrich

L-Alanine methyl ester hydrochloride

99%, for peptide synthesis

Synonym(s):

(S)-2-Aminopropionic acid methyl ester hydrochloride, L-Ala-OMe·HCl

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About This Item

Linear Formula:
CH3CH(NH2)COOCH3 · HCl
CAS Number:
2491-20-5
Molecular Weight:
139.58
Beilstein/REAXYS Number:
3594033
EC Number:
219-652-4
MDL number:
MFCD00063663
UNSPSC Code:
12352209
eCl@ss:
32160406
PubChem Substance ID:
24859397
NACRES:
NA.22

product name

L-Alanine methyl ester hydrochloride, 99%

assay

99%

optical activity

[α]25/D +7.0°, c = 1.6 in methanol

reaction suitability

reaction type: solution phase peptide synthesis

mp

109-111 °C (lit.)

application(s)

peptide synthesis

SMILES string

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

InChI

1S/C4H9NO2.ClH/c1-3(5)4(6)7-2;/h3H,5H2,1-2H3;1H/t3-;/m0./s1

InChI key

IYUKFAFDFHZKPI-DFWYDOINSA-N

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General description

L-Alanine methyl ester hydrochloride also known as L-Ala-OMe·HCl, is a versatile reagent used commonly in solution phase peptide synthesis. It is often used to synthesize dipeptides.

Application

L-Alanine methyl ester hydrochloride can be used as a starting material in the synthesis of alanine isoxazolidide via solution phase peptide synthesis. Additionally, it is used to synthesize N-Fmoc-l-alanyl-l-alanine methyl ester and α-amino acid-based sector block dendrons.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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N-methylation of peptides on selected positions during the elongation of the peptide chain in solution phase
ML Di Gioia
The Journal of Organic Chemistry, 70, 3892-3897 (2005)
Synthesis and gelation properties of a new class of $\alpha$-amino acid-based sector block dendrons
HF Chow
Tetrahedron, 61, 11279-11290 (2005)
The dimethylsulfoxonium methylide as unique reagent for the simultaneous deprotection of amino and carboxyl function of N-Fmoc-?-amino acid and N-Fmoc-peptide esters
M Spinella
Tetrahedron, 69, 2010-2016 (2013)
Hala Bakr El-Nassan et al.
Pharmaceutical research, 35(8), 149-149 (2018-05-31)
To assess the gelation power of N-palmitoyl L-alanine derivatives in injectable oils and to use the best chosen organogel as parenteral implant of granisetron for the treatment of emesis. Twelve N-palmitoyl L-alanine derived organogels were developed and evaluated in terms
Jingwen Luo et al.
Drug development and industrial pharmacy, 45(1), 96-104 (2018-09-11)
This article aims to design low molecular weight chitosan (LMWC)-based conjugates of Rhein (RH) by means of an amino acid linker (Alanine) for improved solubility and enhanced bioavailability. Rhein is a potential candidate for the therapy of kidney disease. However
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