Reaction Between Oxophosphorus Acids and Glycine

Abstract

2-Hydroxyesters of oxophosphorus acids (hypophosphorous, phosphorous and phosphoric) react with glycine to give amidoglycine-H-phosphinate, cyclic phosphoamidoanhydridegl ycine-H-phosphonate and cyclic phosphoamidoanhydrideglycinephosphate. The reaction proceeds easily and in high yields under mild conditions because of the effect of vicinally hydroxy group as intramolecular catalyst on the reactivity of the ester bonds.

Biomimetic synthesis of esters of natural amino acids

“…In our previous paper [10], we have reported that the reaction between 2-hydroxypropyl esters of oxophosphorus acids and glycine in methanol solution produces phosphoamidoacyl phosphates as shown in Fig. 1.…”

“…It has long been known that 2-hydroxy esters of oxophosphorus acids can be used as phosphorylating reagents [6,7]. They are easy to obtain, simple compounds and have been successfully used in the phosphorylation of D-glucose [8], desoxynucleosides [9], and glycine [10].…”

On the Electrophilicity of Cyclic Acylphosphoramidates (CAPAs) Postulated as Intermediates

“…Hence, great effort should be focused on the preparation of pure CAPAs in the future, even though the preparation of Gly-CAPA has been described. [36] It is noteworthy that the reversible conversion between Gly-CAPA 4a and N-pyrophosphoglycine 9a, demonstrated in this work, may provide an alternative path to the in situ generation of CAPAs, which makes investigations of CAPAs feasible in neutral (Figure 6a) or acidic solutions. Because the development of the chemistry of NCAs is more extensive than that of CAPAs, we believe that successful experiences on NCAs can serve as a reference for the chemistry of CAPAs.…”

Investigation of Reaction Mechanism of Amino Acids and Phosphorus Trichloride by 31 P NMR and ESI-MS/MS

“…It is reported that the signal of the analogue of compound 4 ( Table 1, when R＝H), appeared at δ 10.39 using TFA as solvent in 31 P NMR spectroscopy. 33 The literature also reported that, in different solvents, the triphenyldichlorophosphane gave different chemical shifts reflecting different structures, such as ionic forms or non-ionic forms. 22 Therefore, we detected the 31 P NMR spectrum of reaction solution in TFA.…”