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DOI: 10.1055/s-2002-19325
Synthesis and Properties of Glycolaldehyde Di- and Triphosphate
Publication History
Publication Date:
01 February 2007 (online)
Abstract
Use of photolabile acetal protecting groups enables the synthesis of glycolaldehyde di- and triphosphate 4 and 5, which undergo enolisation at significantly lower pH values than glycolaldehyde phosphate 1. At pH > 10, 5 is converted to 1 and inorganic pyrophosphate.
Key words
aldehydes - bioorganic chemistry - ozonolysis - phosphorylations - photochemistry
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References
Compound 4: 1H NMR (500 MHz, D2O, pD 8.0): δ = 3.79 (2 H, dd, J = 4.5, J = 6.5, CH2), 5.04 (1 H, t, J = 4.5, CH); 13C NMR (125 MHz, D2O, pD 8.0): δ = 67.9 (d, J = 5.0), 88.5 (d, J = 9.0); 31P NMR (83 MHz, 10 mM EDTA in D2O, pD 8.0): δ = -9.25 (d, J = 22.0), -5.06 (d, J = 22.0); MS (ES-, CV -15 V): m/z (%) = 237(100), [M3- + 2 H+]-; MS (ES-, CV -25 V): m/z (%) = 237(100), [M3- + 2 H+]-), 219(100), [M3- + 2 H+ - H2O]-); MS (ES-, CV -35 V): m/z (%) = 219(100), [M3- + 2 H+ - H2O]-).
10Compound 5: 1H NMR (300 MHz, D2O, pD 8.5): δ = 3.78 (2 H, dd, J = 4.5, J = 7.5, CH2), 5.04 (1 H, t, J = 4.5, CH); 13C NMR (75 MHz, D2O, pD 8.5): δ = 68.1 (d, J = 5.5), 88.3(brs); 31P NMR (83 MHz, 1 mM EDTA in D2O, pD 9.0): δ = -20.85 (t, J = 19.5), -9.70 (d, J = 19.5), -4.95 (d, J = 19.5); MS (ES-, CV -35V): m/z (%) = 321(20), [M4- + 2 H+ + Na+ - H2O]-), 299(5) [M4- + 3 H+ - H2O]-).