Peptidic α-hydroxy phosphinyls C-terminal modification methodology

NMR studies of the bishydroxy bisphosphonate synthesis from o‐phthalic aldehyde and diethyl phosphite

“…In this group there are some compounds that inhibit enzymes such as renin [3,4], EPSP synthetase [5,6], and HIV protease [7,8].…”

Asymmetric Synthesis of α-Substituted-β-Amino Phosphonates and Phosphinates and β-Amino Sulfur Analogs

“…Thus, a suitable methodology has been developed for modifications at the phosphorus terminus of the a-hydroxy phosphinic moiety in 16 (Scheme 13.21). 56 For the preparation of phosphinodipeptide 107, it was found necessary to protect the b-amino-a-hydroxy phosphonate 16 in order to direct reactions specifically at the phosphorus center and minimize side reactions. Thus, compound 16 was converted to the fully protected oxazolidine derivative by following the special procedure of Garner and Park, 57 wherein it was treated with a large excess of 2,2-dimethoxypropane and the MeOH being produced was continually removed by slow distillation of the reaction mixture.…”

“…Authors also reported the insertion of oxygen and nitrogen at the phosphorus center of intermediate 103. 56 Stowasser et al 58 have also described the synthesis of b-amino-a-hydroxy phosphinopeptide 113 (Scheme 13.22). Phosphinopeptide 113 is a powerful Finally, deprotection of the Boc group and hydrolysis of the ester group gave 113.…”

Conformation of Sterically Hindered 4-Methyl-2-oxo-2-trityl-1,3,2-dioxaphosphorinane in the Solid State and the Solution

“…Additionally, the phosphonic acids and their derivatives may be considered as long life analogues of transition states for tetrahedral intermediates in amide/ester hydrolysis [16]. Among others, these compounds also possess enzyme inhibition properties and consequently they can serve as antibacterial and anticancer drugs [17][18][19][20][21][22][23][24][25][26][27][28][29][30][31]. Phosphorylated alkenes are also synthetically useful [32][33][34][35] and are commonly used in organic synthesis [36][37][38][39][40].…”