70771-89-0Relevant academic research and scientific papers
Structure-property relationship study of n-(hydroxy)peptides for the design of self-assembled parallel β-sheets
Roche, Stéphane P.,Richaud, Alexis D.
, p. 12329 - 12342 (2020/11/10)
The design of novel and functional biomimetic foldamers remains a major challenge in creating mimics of native protein structures. Herein, we report the stabilization of a remarkably short β-sheet by incorporating N-(hydroxy)glycine (Hyg) residues into the backbone of peptides. These peptide- peptoid hybrids form unique parallel β-sheet structures by selfassembly upon hydrogenation. Our spectroscopic and crystallographic data suggest that the local conformational perturbations induced by N-(hydroxy)amides are outweighed by a network of strong interstrand hydrogen bonds.
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.
α-Functionalized Amino Acid Derivatives. A Synthetic Approach of Possible Biogenetic Importance
Herscheid, Jacobus D. M.,Nivard, Rutger J. F.,Tijhuis, Marian W.,Scholten, Henk P. H.,Ottenheijm, Harry C. J.
, p. 1880 - 1885 (2007/10/02)
A new and efficient approach of general applicability to the synthesis of α-functionalized α-amino acid derivatives 3 is described.It is based upon the proposal that the biosynthesis of such compounds might occur via oxidation of an N-acylated amino acid
