3884-90-0Relevant academic research and scientific papers
Nitrone protecting groups for enantiopure N-hydroxyamino acids: Synthesis of N-terminal peptide hydroxylamines for chemoselective ligations
Medina, S. Irene,Wu, Jian,Bode, Jeffrey W.
supporting information; experimental part, p. 3405 - 3417 (2010/08/21)
The synthesis of enantiopure N-benzylidene nitrones of N-hydroxy-α- amino acids and their incorporation using standard Fmoc-based peptide chemistry into solid-supported peptide chains is described. Deprotection and resin cleavage affords N-terminal peptid
5-Hydroxy[1,2]oxazinan-3-ones as potential carbapenem and D-ala-D-ala surrogates
Wolfe, Saul,Akuche, Christiana,Ro, Stephen,Wilson, Marie-Claire,Kim, Chan-Kyung,Shi, Zheng
, p. 915 - 936 (2007/10/03)
The title compounds are amino acids whose nitrogen atom is enclosed in a six-membered cyclic hydroxamate bearing a C5-hydroxyl group. They belong to a proposed new family of antibacterial agents targeted to the penicillin receptor. The glycine and alanine members of the family have been synthesized, as racemates, in seven steps from the four-carbon synthon diketene and the tert-butyl esters of N-hydroxyglycine and N-hydroxyalanine. Numerous alternatives to diketene have also been examined, but these lead mainly to five-membered cyclic hydroxamates. The theoretical considerations that have led to this synthetic programme are discussed in some detail. They include analysis of the structures of natural and unnatural penicillin surrogates, analysis of the penicillin pharmacophore, and a treatment of the chemical reaction with which penicillin blocks bacterial cell wall synthesis. The glycine derivative exhibits marginal but real activity vs. Micrococcus luteus. The alanine derivative, which more closely resembles D-ala-D-ala, is fifty times more active. Two five-membered structural isomers of the glycine derivative are inactive.
Ring-Chain Isomerism of N-(1-Carboxyalkyl)nitrones,I. - C-Aryl-N-(1-carboxyalkyl)nitrones
Kliegel, Wolfgang,Graumann, Juergen
, p. 1545 - 1562 (2007/10/02)
N-(1-Carboxyalkyl)nitrones 3 are prepared by alkylation of aromatic (Z)-aldoximes 1 or by condensation of α-(hydroxyamino)carboxylic acids 2 and aromatic aldehydes.The ring-chain isomerism between the nitrone 3 and the N-hydroxyoxazolidine 4 could not be proved by spectroscopical methods.Acylation of 3 with diphenylborinic acid leads to diphenylboron chelates 5 of the open-chain nitrone form, whereas acylation with carboxylic acids or isocyanate results in the formation of N-(acyloxy)oxazolidones 8.Alkylation of 3 with phenacyl bromide gives the ester 12.
