Acetyl-L-phenylalanine
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Acetyl-L-phenylalanine

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Category
L-Amino Acids
Catalog number
BAT-003873
CAS number
2018-61-3
Molecular Formula
C11H13NO3
Molecular Weight
207.20
Acetyl-L-phenylalanine
IUPAC Name
(2S)-2-acetamido-3-phenylpropanoic acid
Synonyms
N-Acetyl-L-phenylalanine; 2018-61-3; Acetyl-L-phenylalanine; Ac-Phe-OH; acetylphenylalanine; L-N-Acetylphenylalanine
Appearance
White powder
Purity
≥ 99% (HPLC)
Density
1.1878 g/cm3(rough estimate)
Melting Point
158-174 ºC
Boiling Point
346.25°C (rough estimate)
Storage
Store at 2-8°C
InChI
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
Canonical SMILES
CC(=O)NC(CC1=CC=CC=C1)C(=O)O
1. Rational design of aminoacyl-tRNA synthetase specific for p-acetyl-L-phenylalanine
Renhua Sun, Heng Zheng, Zhengzhi Fang, Wenbing Yao Biochem Biophys Res Commun. 2010 Jan 1;391(1):709-15. doi: 10.1016/j.bbrc.2009.11.125. Epub 2009 Nov 26.
The Methanococcus jannaschii tRNA(Tyr)/tyrosyl-tRNA synthetase pair has been engineered to incorporate unnatural amino acids into proteins in Escherichia coli site-specifically. In order to add other unnatural amino acids into proteins by this approach, the amino acid binding site of M. jannaschii tyrosyl-tRNA synthetase need to be mutated. The crystal structures of M. jannaschii tyrosyl-tRNA synthetase and its mutations were determined, which provided an opportunity to design aminoacyl-tRNA synthetases specific for other unnatural amino acids. In our study, we attempted to design aminoacyl-tRNA synthetases being able to deliver p-acetyl-L-phenylalanine into proteins. p-Acetyl-L-phenylalanine was superimposed on tyrosyl in M. jannaschii tyrosyl-tRNA synthetase-tyrosine complex. Tyr32 needed to be changed to non-polar amino acid with shorter side chain, Val, Leu, Ile, Gly or Ala, in order to reduce steric clash and provide hydrophobic environment to acetyl on p-acetyl-L-phenylalanine. Asp158 and Ile159 would be changed to specific amino acids for the same reason. So we designed 60 aminoacyl-tRNA synthetases. Binding of these aminoacyl-tRNA synthetases with p-acetyl-L-phenylalanine indicated that only 15 of them turned out to be able to bind p-acetyl-L-phenylalanine with reasonable poses. Binding affinity computation proved that the mutation of Tyr32Leu and Asp158Gly benefited p-acetyl-L-phenylalanine binding. And two of the designed aminoacyl-tRNA synthetases had considerable binding affinities. They seemed to be very promising to be able to incorporate p-acetyl-L-phenylalanine into proteins in E. coli. The results show that the combination of homology modeling and molecular docking is a feasible method to filter inappropriate mutations in molecular design and point out beneficial mutations.
2. N-Acetyl-l-phenylalanine Racemization during TBTU Amidation: An In-Depth Study for the Synthesis of Anti-Inflammatory 2-( N-Acetyl)-l-phenylalanylamido-2-deoxy-d-glucose (NAPA)
Elisa Sturabotti, Fabrizio Vetica, Giorgia Toscano, Andrea Calcaterra, Andrea Martinelli, Luisa Maria Migneco, Francesca Leonelli Molecules. 2023 Jan 6;28(2):581. doi: 10.3390/molecules28020581.
A thorough study on the amidation conditions of N-acetyl-l-phenylalanine using TBTU and various bases is reported for the synthesis of 2-(N-acetyl)-l-phenylalanylamido-2-deoxy-d-glucose (NAPA), a promising drug for the treatment of joints diseases. TBTU-mediated diastereoselective amidation reaction with 1,3,4,6-tetra-O-acetyl-β-d-glucosamine always gave racemization of N-acetyl-l-phenylalanine. The stereochemical retention under amidation conditions was studied in detail in the presence of difference bases and via other control experiments, evidencing the possibility to reduce racemization using pyridine as base.
3. N-Acetyl-L-phenylalanine
K L Stout, K J Hallock, J W Kampf, A Ramamoorthy Acta Crystallogr C. 2000 Mar 15;56(Pt 3):E100. doi: 10.1107/S0108270100001712. Epub 2000 Mar 15.
The structure of the title compound, C(11)H(13)NO(3), is characterized by a two-dimensional infinite network of intermolecular N-H.O and O-H.O hydrogen bonds.
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