Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
Review
. 2014 May 16;19(5):6349-67.
doi: 10.3390/molecules19056349.

Utilization of acidic α-amino acids as acyl donors: an effective stereo-controllable synthesis of aryl-keto α-amino acids and their derivatives

Lei Wang  1 , Yuta Murai  2 , Takuma Yoshida  1 , Masashi Okamoto  1 , Zetryana Puteri Tachrim  1 , Yasuyuki Hashidoko  1 , Makoto Hashimoto  3
Affiliations
Review

Utilization of acidic α-amino acids as acyl donors: an effective stereo-controllable synthesis of aryl-keto α-amino acids and their derivatives

Lei Wang et al. Molecules. .

Abstract

Aryl-keto-containing α-amino acids are of great importance in organic chemistry and biochemistry. They are valuable intermediates for the construction of hydroxyl α-amino acids, nonproteinogenic α-amino acids, as well as other biofunctional components. Friedel-Crafts acylation is an effective method to prepare aryl-keto derivatives. In this review, we summarize the preparation of aryl-keto containing α-amino acids by Friedel-Crafts acylation using acidic α-amino acids as acyl-donors and Lewis acids or Brönsted acids as catalysts.

PubMed Disclaimer

Conflict of interest statement

The authors declare no conflict of interest.

Figures

Scheme 1
Scheme 1
Synthesis and application of aryl-keto α-amino acids.
Scheme 2
Scheme 2
Preparation of aryl-keto α-amino acid derivatives by Claisen condensation.
Scheme 3
Scheme 3
Cross-coupling reaction: a useful method to construct aryl-keto α-amino acids.
Scheme 4
Scheme 4
Synthesis of α-benzoyl-L-alanine and α-benzoyl-D-alanine from acetamidomalonate.
Scheme 5
Scheme 5
Preparation of aryl-keto α-amino acids from non-amino acid derivatives.
Scheme 6
Scheme 6
α- and β- amino acids derived from aspartic anhydrides.
Scheme 7
Scheme 7
Acylation direction of phthalylaspartic anhydride in Friedel-Crafts acylation.
Scheme 8
Scheme 8
Preparation of ADTN bis(methyl ether) from veratrole by Friedel-Crafts acylation.
Scheme 9
Scheme 9
Preparation of homotyrosine derivative from 2-chloroanisole.
Scheme 10
Scheme 10
L-Aspartic anhydride hydrochloride as the acyl-donor in Friedel–Crafts acylation.
Scheme 11
Scheme 11
HF as catalyst in Friedel-Crafts acylation.
Scheme 12
Scheme 12
Synthesis of trifluoromethyldiazirinyl homophenylalanine by Friedel-Crafts acylation.
Scheme 13
Scheme 13
Synthesis of homotyrosines by Friedel-Crafts acylation with TfOH.
Scheme 14
Scheme 14
Synthesis of bishomophenylalanine and diazirinyl derivative by Friedel-Crafts acylation.
Scheme 15
Scheme 15
Synthesis of bishomotyrosine by Friedel-Crafts acylation with TfOH.
Scheme 16
Scheme 16
Previous synthesis of p-benzoyl-L-phenylalanine from p-methylbenzophenone.
Scheme 17
Scheme 17
Synthesis of benzophenone based α-amino acid derivatives and two photophores based structures by Friedel-Crafts acylation with TfOH.
Scheme 18
Scheme 18
Friedel–Crafts reaction and hydrogen/deuterium exchange with TfOD.
See this image and copyright information in PMC

Similar articles

See all similar articles

Cited by

References

    1. Hartung W.H., Dittrich T.T., Chang Y.T. β-Arylserine ethyl esters. J. Am. Chem. Soc. 1953;75:238–239. doi: 10.1021/ja01097a513. - DOI
    1. Hernández D., Vilar G., Riego E., Cañedo L.M., Cuevas C., Albericio F., Álvarez M. Synthesis of IB-01211, a cyclic peptide containing 2,4-concatenated thia- and oxazoles, via Hantzsch macrocyclization. Org. Lett. 2007;9:809–811. - PubMed
    1. Ojika M., Inukai Y., Kito Y., Hirata M., Iizuka T., Fudou R. Miuraenamides: Antimicrobial cyclic depsipeptides isolated from a rare and slightly halophilic myxobacterium. Chem. Asian J. 2008;3:126–133. doi: 10.1002/asia.200700233. - DOI - PubMed
    1. Vanderhaeghe H., Parmentier G. The structure of factor S of staphylomycin. J. Am. Chem. Soc. 1960;82:4414–4422. doi: 10.1021/ja01501a070. - DOI
    1. Yamaguchi M., Yamaki H., Shinoda T., Tago Y., Suzuki H., Nishimura T., Yamaguchi H. The mode of antifungal action of (S)2-amino-4-oxo-5-hydroxypentanoic acid, RI-331. J. Antibiot. 1990;43:411–416. doi: 10.7164/antibiotics.43.411. - DOI - PubMed

Publication types

LinkOut - more resources