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Synthesis of new functionalized aziridine-2-and azetidine-3-carboxylic acid derivatives of potential interest for biological and foldameric applications

(2011) AMINO ACIDS. 41(3). p.541-558
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Abstract
short synthesis of alkyl 2-(bromomethyl)aziridine-2-carboxylates and alkyl 3-bromoazetidine-3-carboxylates was developed involving amination, bromination, and base-induced cyclization of alkyl 2-(bromomethyl)acrylates. The aziridines are the kinetically favored cyclization products and could be transformed into 3-bromoazetidine-3-carboxylic acid derivatives via thermal isomerization. The new small-membered azaheterocyclic alpha- and beta-amino acid derivatives contain a bromo-substituted carbon center as a useful moiety for functionalization. Transformation of these functionalized azaheterocycles via nucleophilic substitution with carbon, sulfur, oxygen, and nitrogen nucleophiles and via elaboration of the amino and carboxyl group provided a broad range of new conformationally constrained aziridine-2- and azetidine-3-carboxylic acid derivatives, which are of interest from a biological point-of-view as well as for applications in the field of foldamers.
Keywords
Aziridine-2-carboxylic acids, CHEMISTRY, Azetidine-3-carboxylic acids, beta-Amino acids, alpha-Amino acids, Conformational constraint, RING TRANSFORMATION, INTERMEDIATE AZIRIDINIUM SALTS, STEREOSPECIFIC ANIONIC-POLYMERIZATION, BETA-AMINO ACIDS, INHIBITORS, REACTIVITY, 2-(CYANOMETHYL)AZIRIDINES, ANTIBACTERIAL AGENTS, PEPTIDES

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Citation

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MLA
Žukauskaitė, Asta et al. “Synthesis of New Functionalized Aziridine-2-and Azetidine-3-carboxylic Acid Derivatives of Potential Interest for Biological and Foldameric Applications.” AMINO ACIDS 41.3 (2011): 541–558. Print.
APA
Žukauskaitė, A., Mangelinckx, S., Buinauskaite, V., Sackus, A., & De Kimpe, N. (2011). Synthesis of new functionalized aziridine-2-and azetidine-3-carboxylic acid derivatives of potential interest for biological and foldameric applications. AMINO ACIDS, 41(3), 541–558.
Chicago author-date
Žukauskaitė, Asta, Sven Mangelinckx, Vida Buinauskaite, Algirdas Sackus, and Norbert De Kimpe. 2011. “Synthesis of New Functionalized Aziridine-2-and Azetidine-3-carboxylic Acid Derivatives of Potential Interest for Biological and Foldameric Applications.” Amino Acids 41 (3): 541–558.
Chicago author-date (all authors)
Žukauskaitė, Asta, Sven Mangelinckx, Vida Buinauskaite, Algirdas Sackus, and Norbert De Kimpe. 2011. “Synthesis of New Functionalized Aziridine-2-and Azetidine-3-carboxylic Acid Derivatives of Potential Interest for Biological and Foldameric Applications.” Amino Acids 41 (3): 541–558.
Vancouver
1.
Žukauskaitė A, Mangelinckx S, Buinauskaite V, Sackus A, De Kimpe N. Synthesis of new functionalized aziridine-2-and azetidine-3-carboxylic acid derivatives of potential interest for biological and foldameric applications. AMINO ACIDS. 2011;41(3):541–58.
IEEE
[1]
A. Žukauskaitė, S. Mangelinckx, V. Buinauskaite, A. Sackus, and N. De Kimpe, “Synthesis of new functionalized aziridine-2-and azetidine-3-carboxylic acid derivatives of potential interest for biological and foldameric applications,” AMINO ACIDS, vol. 41, no. 3, pp. 541–558, 2011.
@article{1864225,
  abstract     = {short synthesis of alkyl 2-(bromomethyl)aziridine-2-carboxylates and alkyl 3-bromoazetidine-3-carboxylates was developed involving amination, bromination, and base-induced cyclization of alkyl 2-(bromomethyl)acrylates. The aziridines are the kinetically favored cyclization products and could be transformed into 3-bromoazetidine-3-carboxylic acid derivatives via thermal isomerization. The new small-membered azaheterocyclic alpha- and beta-amino acid derivatives contain a bromo-substituted carbon center as a useful moiety for functionalization. Transformation of these functionalized azaheterocycles via nucleophilic substitution with carbon, sulfur, oxygen, and nitrogen nucleophiles and via elaboration of the amino and carboxyl group provided a broad range of new conformationally constrained aziridine-2- and azetidine-3-carboxylic acid derivatives, which are of interest from a biological point-of-view as well as for applications in the field of foldamers.},
  author       = {Žukauskaitė, Asta and Mangelinckx, Sven and Buinauskaite, Vida and Sackus, Algirdas and De Kimpe, Norbert},
  issn         = {0939-4451},
  journal      = {AMINO ACIDS},
  keywords     = {Aziridine-2-carboxylic acids,CHEMISTRY,Azetidine-3-carboxylic acids,beta-Amino acids,alpha-Amino acids,Conformational constraint,RING TRANSFORMATION,INTERMEDIATE AZIRIDINIUM SALTS,STEREOSPECIFIC ANIONIC-POLYMERIZATION,BETA-AMINO ACIDS,INHIBITORS,REACTIVITY,2-(CYANOMETHYL)AZIRIDINES,ANTIBACTERIAL AGENTS,PEPTIDES},
  language     = {eng},
  number       = {3},
  pages        = {541--558},
  title        = {Synthesis of new functionalized aziridine-2-and azetidine-3-carboxylic acid derivatives of potential interest for biological and foldameric applications},
  url          = {http://dx.doi.org/10.1007/s00726-011-0879-1},
  volume       = {41},
  year         = {2011},
}

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