77821-22-8Relevant articles and documents
Access to Enantiopure α-Hydrazino Acids for N-Amino Peptide Synthesis
Kang, Chang Won,Sarnowski, Matthew P.,Elbatrawi, Yassin M.,Del Valle, Juan R.
, p. 1833 - 1841 (2017/02/10)
Backbone N-methylation of α-peptides has been widely employed to enhance the bioavailability and bioactivity of parent sequences. Heteroatomic peptide amide substituents have received less attention due, in part, to the lack of practical synthetic strategies. Here, we report the synthesis of α-hydrazino acids derived from 19 out of the 20 canonical proteinogenic amino acids and demonstrate their use in the solid-phase synthesis of N-amino peptide derivatives.
Stabilisation of peptide foldamers in an aqueous medium by incorporation of azapeptide building blocks
Hetenyi, Anasztazia,Toth, Gabor K.,Somlai, Csaba,Vass, Elemer,Martinek, Tamas A.,Fueloep, Ferenc
experimental part, p. 10736 - 10741 (2010/04/30)
Stable foldamers in water: Helical peptidic foldamers including H12 and H10/12 helices were constructed and stabilised in water. The foldamers' extra rigidity stems from the strong hydrogen bonding network of the azapeptide groups (see graphic).
N-alkyloxycarbonyl-3-aryloxaziridines: Their preparation, structure, and utilization as electrophilic amination reagents
Vidal, Joelle,Damestoy, Stephanie,Guy, Laure,Hannachi, Jean-Christophe,Aubry, Andre,Collet, Andre
, p. 1691 - 1709 (2007/10/03)
This paper reports the synthesis of a series of N-protected oxaziridines (N-Moc, Boc, Z or Fmoc) and discusses their ability to deliver their N-alkoxycarbonyl fragment to amines, enolates, sulfur, and phosphorus nucleophiles (electrophilic amination). These oxaziridines are prepared by oxidation of the corresponding imines with oxone or anhydrous MCPBA lithium salt as the source of oxygen. They transfer their N-protected fragment to primary and secondary amines to give protected hydrazines in fair to excelent yield. The nitrogen transfer to free amino acids (in form of their R4N+ salts) is particularly fast, even at low temperature, providing L (or D) N-protected α-hydrazino acids. Enolates are C-aminated to give N-protected α-amino ketones, esters, or amides in modest yield, due to a side aldol reaction of the unreacted enolate with the released benzaldehyde. With tertiary amines (Et3N), sulfides (PhSMe), and phosphines (Ph3P), amination and oxidation proceed in a parallel way; the amount of amination product increases when the temperature is lowered (kinetic control). Some of the factors that can orient the oxaziridine reactivity towards amination or oxidation of nucleophiles are considered.
Electrophilic Amination: Preparation and Use of N-Boc-3-(4-cyanophenyl)oxaziridine, a New Reagent That Transfers a N-Boc Group to N- and C-Nucleophiles
Vidal, Joelle,Guy, Laure,Sterin, Sebastien,Collet, Andre
, p. 4791 - 4793 (2007/10/02)
We describe the preparation of the title compound 2b via aza-Wittig reaction of N-Boc-triphenyliminophosphorane (6) with 4-cyanobenzaldehyde followed by Oxone oxidation of the resulting imine 5b.Oxaziridine 2b is a stable, crystalline solid, which transfers under mild conditions its N-Boc fragment to primary and secondary amines (to give Nβ-Boc-hydrazines) and enolates (to give N-Boc-amino drivatives).
