Phosphonic acid analogs

Lejczak, B., Kafarski, P., Soroka, M., and Mastalerz, P., Synthesis of the phosphonic acid analog of serine, Synthesis, 577,1984. 

Isocyanomethyl)phosphonate 97 is also a beneficial pronucleophile leading to optically active (l-aminoalkyl)phosphonic acids, phosphonic acid analogs of a-amino acids via tra s-5-alkyl-2-oxazoline-4-phosphonates 98 (E = PO(OPh)2, Sch. 25) [50]. ... 

The phosphonic acid analog of NSAID (Non-Steroidal Anti-Inflammatory Drug) diclofenac was successfully synthesized in the laboratory of B. Mugrage using a novel acid catalyzed Arbuzov reaction as the key step followed by a TMSBr promoted dealkylation. It needs to be pointed out that the nucleophilic attack takes place on the ortho-quinonoid intermediate in a non-SN2 process. 

Mugrage, B., Diefenbacher, C., Somers, J., Parker, D. T., Parker, T. Phosphonic acid analogs of diclofenac an Arbuzov reaction of... 

Hullar. T.L.. Pyridoxal phosphate. Part 1. Phosphonic acid analogs of pyridoxal phosphate. Synthesis via Wittig reactions and enzymic evaluation, J. Med. Chem., 12, 58, 1969. 

Coutrot, P., Grison, C., and Lecouvey, M., Preparation of the phosphonic acid analog of 3-deoxy-D-manno-2-octulosonic acid (KDO), Tetrahedron Lett., 37, 1595, 1996. 

Rogers, R.S., and Stern. M.K., An improved synthesis of the phosphonic acid analog of tryptophan, Synlett, 708, 1992. 

Displacing the chlorine of 454a with phosphonate provides ready access to the isosteric phosphonic acid analog 474 of glycerol-3-phosphate. This (5)-enantiomer is a growth inhibitor of Escherichia coli strain 8 and Bacillus subtilus BD strains 170 and 1005 [116]. 

The possibility of the natural existence of phosphonic acid analogs of lecithins prompted Baer and Stanacev (1965b) to synthesize such compounds, which they felt... 

The occurrence of the phosphonic acid analogs of ethanolamine phosphate, serine phosphate, and choline phosphate, the three major constituents of phospholipids, has been established by Kittredge et al. (1967) in the sea anemone, Anthopleura xanthogrammica. They isolated and characterized 2-methylaminoethylphosphonic acid (XXXVII) and 2-trimethylaminoethylphosphonic acid (XXXVIII). 

The coupling of lower carbohydrates with dimethyl 3-bromopropenyl-2-phosphonate in water generated phosphonic acid analogs of both KDN and N-acetyl neuraminic acid by using the indium-mediated aUylation (Scheme 4.10). ... 

Mazur, A., Tropp, B. E., and Engel R. (1984) Isosteres of natural phosphates. 11. Synthesis of a phosphonic acid analog of an oligonucleotide. Tetrahedron 40, 3949-3956. 

Various cyclic phosphonate esters 36 and 37 have been described previously as products from the HHT reaction of 25 with the appropriate cyclic phosphite. A complementary method has also been developed from the V-protected phosphonyl chloride 84, which was readily prepared from the corresponding phosphonic acid 83. Subsequent reaction of 84 with the appropriate diol produced the cyclic phosphonate esters 85 (63). Higher homologs of 85 have also been prepared from the analogous propane or butane diols. 

The related planar pyrrole analog 118 has also been prepared (2) from either ethyl or benzyl pyrrole-2-carboxylate 116. Direct alkylation with diethyl phosphonomethyl triflate (70) and base produced the N-phosphonomethylpyrrole 2-carboxylate 117, which was deprotected with trimethylsilyl bromide and saponified to the corresponding phosphonic acid 118. 

Chan T-H, Xin Y-C, von Itzstein M (1997) Synthesis of phosphonic add analogs of siaUc acids (Neu5Ac and KDN) as potential sialidase inhibitors. J Org Chem 62 3500-3504 Chand P, Kotian PL, Dehghani A, El-Kattan Y, Lin T-H, Hutchison TL, Babu YS, Bantia S, Elliott AJ, Montgomery JA (2001) Systematic structure-based design and stereoselective synthesis of novel multisubstituted cyclopentane derivatives with potent antiinfluenza activity. J Med Chem 44 4379 392... 

Fluorinated phosphinic and phosphonic acid derivatives Perfluoro derivatives of alkyl phosphonic acid CnF2n+1-P(0)(0H)2 and alkyl phosphinic acid CnF2n+i(CmF2m+1)-P(0)0H (n = m or n m) shown with their general structural formulae in Fig. 2.11.29(1) and (II) were examined by negative ESI- and APCI-FIA-MS. These anionic surfactant compounds contained perfluoro alkyl chains [2,22,25]. By analogy with their behaviour in the TSI-FIA-MS(—) process [25], the phosphonic acid formed [M — H] ions at m/z 399 and 499... 

The methodology of the catalytic asymmetric aldol reaction has been further extended to the aldol-type condensation of (isocyanomethyl)phosphonates (12) with aldehydes, providing a useful method for the synthesis of optically active (l-aminoalkyl)phosphonic acids, which are a class of biologically interesting phosphorous analogs of a-amino acids (Scheme 8B1.6) [21,22], Higher enantioselectivity and reactivity are obtained with diphenyl ester 12b than with diethyl ester 12a (Table 8B1.6). 

P. A. Bartlett and M. A. Giangiordano, Transition state analogy of phosphonic acid peptide inhibitors of pepsin, /. Org. Chem. 1996, 61, 3433-3438. 

One of the second type of inhibitor analogs which cause a time-dependent inactivation of alanine racemase is (l-aminoethyl)phosphonic acid, the phosphonate analog of alanine (Ala-P). Ala-P effectively and specifically inactivates alanine racemases from Grampositive bacteria (Bacillus, Staphylococcus, Streptococcus), and serves as a reversible inhibitor of Gram-negative bacterial (Escherichia, Salmonella) alanine racemase.47 53 The mechanism of inhibition was studied with B. stearothermophihis alanine racemase.47 The d- or L-Ala-P leads to an E-I complex with a Ki value of 1 mM, then is slowly isomerized (A nac<=6-9 min-1) to a stoichiometric enzyme complex (E-I ). The Ed dissociates extremely slowly with the... 

Herbicidal properties of this compound as a commercially synthesized ammonium salt (glufosinate or HOE 39866) were first reported in 1977 ill41. This herbicide is presently marketed as BASTA by Hoechst AG. Some phosphonic and phosphinic acid analogs of glutamic acid have been known since 1959 to be inhibitors of glutamine synthetase (GS) (115). but not until 1972 was phosphinothricin found to be a potent inhibitor of GS activity (113)(Figure... 

The reaction of 0-acyl thiohydroxamates with tris(phenylthio)phosphorus, initiated by adventitious oxygen at room temperature, leads in the first instance to alkylbis(phenylthio)phosphines (Scheme 2) by a chain mechanism. Combination of the latter with the disulfide by product affords a phosphotus(V) species which on woik-up gives a]kylbis(phenylduo)phosphonates (Scheme 2 and equation 38) widh moderate to good yields. lliis reaction sequence provides a convenient meduxl for die overall transformation of a carboxylic acid into a readily hydrolyzable ester of the analogous phosphonic acid. 

---