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273910

Sigma-Aldrich

N,N-Dimethyl-L-phenylalanine

99%, for peptide synthesis

Synonym(s):

(2S)-2-(Dimethylamino)-3-phenylpropanoic acid, N,N-Dimethylphenylalanine

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About This Item

Linear Formula:
C6H5CH2CH[N(CH3)2]CO2H
CAS Number:
17469-89-5
Molecular Weight:
193.24
Beilstein/REAXYS Number:
2966581
MDL number:
MFCD00082539
UNSPSC Code:
12352209
eCl@ss:
32160406
PubChem Substance ID:
24856552
NACRES:
NA.22

product name

N,N-Dimethyl-L-phenylalanine, 99%

Quality Level

100

assay

99%

form

powder

optical activity

[α]20/D +77°, c = 1.3 in H2O

reaction suitability

reaction type: solution phase peptide synthesis

mp

225-227 °C (lit.)

application(s)

peptide synthesis

SMILES string

CN(C)[C@@H](Cc1ccccc1)C(O)=O

InChI

1S/C11H15NO2/c1-12(2)10(11(13)14)8-9-6-4-3-5-7-9/h3-7,10H,8H2,1-2H3,(H,13,14)/t10-/m0/s1

InChI key

HOGIQTACRLIOHC-JTQLQIEISA-N

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Application

N,N-Dimethyl-L-phenylalanine is commonly used to prepare Cu(II)-L-amino acid complex, which is a chiral mobile phase additive for the resolution of enantiomers. It can also be used in the total synthesis of (−)-paliurine E and almazole D.

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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Non-ionic surfactant modified ligand exchange chromatography using copper (II) complex of N, N-dimethyl-l-phenylalanine as the chiral additive for enantioselective amino acids separation.
Dimitrova P and Bart H J
Analytica Chimica Acta, 663(1), 109-116 (2010)
Total Synthesis of the Cyclopeptide Alkaloid Paliurine E. Insights into Macrocyclization by Ene? Enamide RCM.
Toumi M, et al.
The Journal of Organic Chemistry, 73(4), 1270-1281 (2008)
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Different approaches of impregnation for resolution of enantiomers of atenolol, propranolol and salbutamol using Cu (II)-l-amino acid complexes for ligand exchange on commercial thin layer chromatographic plates.
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