Phosphonates as analogues of natural phosphates

R Engel - Chemical Reviews, 1977 - ACS Publications
During the past 15 years there has developed significant in-terest in the preparation and
investigation of phosphonic acids and their derivatives which might be considered to be …

Some influences of fluorine in bioorganic chemistry

HS Rzepa - Chemical Communications, 1997 - pubs.rsc.org
Some influences of fluorine in bioorganic chemistry Page 1 O O R′′ R O O R′′ R O O R′′
R HO O R′′ R 1 R = R′′ = H mp = 72 C 2 R = H, R′′ = F mp = 73 C 3 R = R′′ = F mp …

Synthesis of monofluoro-and difluoro-methylenephosphonate analogues of sn-glycerol-3-phosphate as substrates for glycerol-3-phosphate dehydrogenase and the X …

J Nieschalk, AS Batsanov, D O'Hagan, J Howard - Tetrahedron, 1996 - Elsevier
The synthesis of the cyclohexylammonium salts of (1RS, 3S)-3, 4-dihydroxy-1-
fluorobutylphosphonic acid 3 and (S)-difluoro-3, 4-dihydroxybutylphosphonic acid 4 is …

The preparation of (EtO) 2P (O) CFHZnBr and (EtO) 2P (O) CFHCu and their utility in the preparation of functionalized α-fluorophosphonates

X Zhang, W Qiu, DJ Burton - Tetrahedron letters, 1999 - Elsevier
The organometallic reagent,(EtO) 2P (O) CFHZnBr, was generated in situ in excellent yields
via the reaction of (EtO) 2P (O) CFHBr with zinc metal. Metathesis with Cu (I) Br gave (EtO) …

Monofluorophosphonates as phosphate mimics in bioorganic chemistry: a comparative study of CH2-, CHF-and CF2-phosphonate analogues of sn-glycerol-3 …

J Nieschalk, D O'Hagan - Journal of the Chemical Society, Chemical …, 1995 - pubs.rsc.org
The synthesis of the cyclohexylammonium salts of 3-(S), 4-dihydroxy-1 (R, S)-
fluorobutylphosphonic acid 3 and 1, 1-difluoro-3-(S), 4-dihydroxybutylphosphonic acid 4 is …

Dehydrogenation of a phosphonate substrate analogue by glycerol 3-phosphate dehydrogenase

PR Adams, R Harrison, TD Inch - Biochemical Journal, 1974 - ncbi.nlm.nih.gov
Abstract S-(+)-3, 4-Dihydroxybutylphosphonic acid, an isosteric analogue of sn-glycerol 3-
phosphate, was synthesized stereospecifically and shown to be an effective substrate for …

Phosphonomethyl analogues of phosphate ester glycolytic intermediates

HBF Dixon, MJ Sparkes - Biochemical Journal, 1974 - portlandpress.com
Analogues of dihydroxyacetone phosphate and of 3-phosphoglycerate were made in which
the phosphate group,–O–PO3H2, is replaced by the phosphonomethyl group,–CH2 …

The interaction of phosphonate and homophosphonate analogues of 3-deoxy-D-arabino heptulosonate 7-phosphate with 3-dehydroquinate synthetase from …

P Le Maréchal, C Froussios, M Level… - … and Biophysical Research …, 1980 - Elsevier
Phosphonate and homophosphonate analogues of 3-deoxy-D-arabino heptulosonate 7-
phosphate and D-gluco heptulosonate 7-phosphate behave as competitive inhibitors of 3 …

Practical synthesis of 4-hydroxy-3-oxobutylphosphonic acid and its evaluation as a bio-isosteric substrate of DHAP aldolase

HL Arth, WD Fessner - Carbohydrate research, 1997 - Elsevier
An efficient four step synthesis of the title compound 4-hydroxy-3-oxobutylphosphonate (2)
has been developed based on inexpensive 4-ethoxy-1-hydroxybutane-2-one using an …

Isosteres of natural phosphates. 10. synthesis of analogues related to glycerol 3-phosphate

N Lalinde, BE Tropp, R Engel - Tetrahedron, 1983 - Elsevier
We have synthesized a pair of diastereoisomers of 1, 3, 4-trihydroxybutyl-1-phosphonic acid.
Both bear the same absolute configuration as sn-glycerol 3-phosphate at the 3-position, but …