62056-93-3Relevant academic research and scientific papers
Group-assisted purification (gap) for protection of amino acids using n-phosphonyl functional groups
An, Guanghui,Seifert, Cole,Sun, Hao,Pan, Yi,Li, Guigen
, p. 344 - 356 (2015)
Various phosphonyl halides have been synthesized and utilized as protection groups for amino acids. The protection synthesis was performed via GAP (Group-Assisted Purification) procedure under convenient conditions without the use of column chromatography
The use of phosphinamide N-protecting groups in the diastereoselective reduction of ketones
Palmer, Matthew J.,Studley, John R.,Walsgrove, Tim C.,Wills, Martin
, p. 8827 - 8840 (2007/10/03)
The phosphinamide N-protecting group is demonstrated to be an effective directing group for diastereoselective reductions of proximal ketones. A range of methods for the preparation of the requisite α-amino ketones substrates are described.
Application of Diphenylphosphinic Carboxylic Mixed Anhydrides to Peptide Synthesis.
Ramage, Robert,Hopton, David,Parrott, Maxwell J.,Richardson, Reginald S.,Kenner, George W.,Moore, Geoffrey A.
, p. 461 - 470 (2007/10/02)
Diphenylphosphinic carboxylic mixed anhydrides formed in situ from Nα-protected amino acids and diphenylphosphinic chloride have been critically evaluated in peptide synthesis.Wherever possible, 32.4 MHz 31P n.m.r. spectroscopy has been employed to follow the rates of both mixed anhydride formation and aminolysis.
Phosphinamides: A New Class of Amino Protecting Groups in Peptide Synthesis
Ramage, Robert,Hopton, David,Parrott, Maxwell J.,Kenner, George W.,Moore, Geoffrey A.
, p. 1357 - 1370 (2007/10/02)
Nα-Diphenylphosphinyl protected α-amino acids have been prepared from the corresponding methyl or benzyl esters using diphenylphosphinic chloride-N-methylmorpholine followed by mild alkaline hydrolysis or catalytic hydrogenolysis, respectively.The suitability of these derivatives for use in amide bond forming reactions and their stability during the customary manipulations of peptide synthesis have been exhaustively examined.Acid-catalysed removal of the diphenylphosphinyl group has also been studied, with the aid of 32.4 MHz 32P n.m.r. spectroscopy, and compatability of cleavage with tryptophan and methionine residues - in the absence of scavengers - has been demonstrated by the synthesis of the partially protected C-terminal tetrapeptide of gastrin, Cl(1-)H2(1+)Trp-Met-Asp(Ot-Bu)-PheNH2.
