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857459

Sigma-Aldrich

N-Acetyl-L-phenylalanine

ReagentPlus®, 99%

Synonym(s):

(+)-N-Acetylphenylalanine, (S)-2-Acetamido-3-phenylpropanoic acid

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About This Item

Linear Formula:
C6H5CH2CH(NHCOCH3)CO2H
CAS Number:
2018-61-3
Molecular Weight:
207.23
EC Number:
217-959-8
MDL number:
MFCD00063158
UNSPSC Code:
12352209
eCl@ss:
32160406
PubChem Substance ID:
24888445
NACRES:
NA.22

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Quality Level

100

product line

ReagentPlus®

assay

99%

form

powder

optical activity

[α]22/D +40.0°, c = 1 in methanol

reaction suitability

reaction type: C-H Activation
reaction type: solution phase peptide synthesis
reagent type: ligand
reaction type: Peptide Synthesis

mp

171-173 °C (lit.)

application(s)

peptide synthesis

functional group

amine
carboxylic acid

SMILES string

CC(=O)N[C@@H](Cc1ccccc1)C(O)=O

InChI

1S/C11H13NO3/c1-8(13)12-10(11(14)15)7-9-5-3-2-4-6-9/h2-6,10H,7H2,1H3,(H,12,13)(H,14,15)/t10-/m0/s1

InChI key

CBQJSKKFNMDLON-JTQLQIEISA-N

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General description

N-Acetyl-L-phenylalanine is an acetyl analog of L-phenylalanine. It is widely used as a reactant to synthesize methyl or ethyl esters of N-acetyl-L-phenylalanine, which are employed as versatile building blocks in peptide synthesis.[1][2]

Application

N-Acetyl-L-phenylalanine can be used as a reactant to synthesize:
  • N-acetyl phenylalanine methyl ester by esterification reaction with methanol using Mukaiyama′s reagent.[2]
  • Acetylaminocyclohexane propanoic acid by rhodium-catalyzed hydrogenation reaction.[3]

Legal Information

ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany

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Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
MKCQ2845
MKCJ8418
MKBX6307V
MKBQ7814V
MKBH5259

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Sigma-Aldrich

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N-Acetyl-L-methionine

Surfactant-protease complex as a novel biocatalyst for peptide synthesis in hydrophilic organic solvents
Okazaki S, et al.
Enzyme and Microbial Technology, 26(2-4), 159-164 (2000)
Microwave-assisted esterification of N-Acetyl-L-Phenylalanine using modified mukaiyama?s reagents: A new approach involving ionic liquids
Zhao H, et al.
International Journal of Molecular Sciences, 9(1), 33-44 (2008)
Efficient and practical arene hydrogenation by heterogeneous catalysts under mild conditions
Maegawa T, et al.
Chemistry?A European Journal , 15(28), 6953-6963 (2009)
Corinna Neuber et al.
Analytical chemistry, 86(18), 9065-9073 (2014-08-20)
Sphingosine 1-phosphate (S1P), a bioactive lipid involved in various physiological processes, can be irreversibly degraded by the membrane-bound S1P lyase (S1PL) yielding (2E)-hexadecenal and phosphoethanolamine. It is discussed that (2E)-hexadecenal is further oxidized to (2E)-hexadecenoic acid by the long-chain fatty
Anton V Yakovenko et al.
The Journal of organic chemistry, 72(9), 3223-3231 (2007-03-28)
Bisurea calix[4]arenes 1 and 2 possessing L-amino acid moieties at the lower rim were synthesized by reaction of the methyl esters of glycine, L-alanine, or L-isoleucine with the appropriate isocyanate (12 or 13), obtained with a safe and efficient Curtius
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Chromatograms

application for HPLC

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