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

Asta Žukauskaitė UGent, Sven Mangelinckx UGent, Vida Buinauskaite UGent, Algirdas Sackus and Norbert De Kimpe UGent (2011) AMINO ACIDS. 41(3). p.541-558
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.
Please use this url to cite or link to this publication:
author
organization
year
type
journalArticle (original)
publication status
published
subject
keyword
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
journal title
AMINO ACIDS
Amino Acids
volume
41
issue
3
pages
541 - 558
Web of Science type
Article
Web of Science id
000292741700002
JCR category
BIOCHEMISTRY & MOLECULAR BIOLOGY
JCR impact factor
3.248 (2011)
JCR rank
115/286 (2011)
JCR quartile
2 (2011)
ISSN
0939-4451
DOI
10.1007/s00726-011-0879-1
language
English
UGent publication?
yes
classification
A1
copyright statement
I have transferred the copyright for this publication to the publisher
id
1864225
handle
http://hdl.handle.net/1854/LU-1864225
date created
2011-08-01 14:36:25
date last changed
2011-08-03 14:54:10
@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       = {\v{Z}ukauskait\.{e}, Asta and Mangelinckx, Sven and Buinauskaite, Vida and Sackus, Algirdas and De Kimpe, Norbert},
  issn         = {0939-4451},
  journal      = {AMINO ACIDS},
  keyword      = {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},
}

Chicago
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.
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.
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.
MLA
Žukauskaitė, Asta, Sven Mangelinckx, Vida Buinauskaite, 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.