Payne oxidation

P. Koll and D. Eisermann, 1,6-Anhydrofuranoses. 20. Synthesis of two 1,6 2,3-dianhydrohexofuranoses by Payne oxidation of l,6-anhydro-5-0-benzoyl-2,3-dideoxy-/l-D-eryt/jro-hex-2-enofuranose and 1,6-anhydro-5-0-benzoyl-2,3-dideoxy-a-L-tAreo-hex-2-enofuranose, J. Carbohydr. Chem., 7 (1988) 757-771. 

MCPBA is the reagent most commonly used for alkene epoxidation. Payne oxidation (H O / CUjCN) is a convenient and inexpensive alternative. In the course of a study of the enantioselective enzymatic hydrolysis of 6, Takeshi Sugai of Keio University has described Tetrahedron Lett. 2007, 48, 979) a practical procedure for multigram Payne epoxidation of 5. 

W. J. Payne, in Denitrification, Nitrification and Atmospheric Nitrons Oxide, ed. C. C. Delwiche,... 

Sharpless and Masumune have applied the AE reaction on chiral allylic alcohols to prepare all 8 of the L-hexoses. ° AE reaction on allylic alcohol 52 provides the epoxy alcohol 53 in 92% yield and in >95% ee. Base catalyze Payne rearrangement followed by ring opening with phenyl thiolate provides diol 54. Protection of the diol is followed by oxidation of the sulfide to the sulfoxide via m-CPBA, Pummerer rearrangement to give the gm-acetoxy sulfide intermediate and finally reduction using Dibal to yield the desired aldehyde 56. Homer-Emmons olefination followed by reduction sets up the second substrate for the AE reaction. The AE reaction on optically active 57 is reagent... 

Crescenzi AMV, KS Dodgson, GF White, WJ Payne (1985) Initial oxidation and subsequent desulphation of propan-2-yl sulphate by Pseudomonas syringae strain GG. J Gen Microbiol 131 469-477. 

Yeadon, M., Darley-Usmar, V., Payne, A. N. (1991a). Mechanism of oxidant injury in isolated, perfused, ventilated guinea-pig lungs induced by hydrogen peroxide. Am. Rev. Resp. Dis. 143, A581. 

Clem, P. G. Jeon, N.-L. Nuzzo, R. G. Payne, D. A. 1997. Monolayer-mediated deposition of tantalum (V) oxide thin film structures from solution precursors. J. Am. Ceram. Soc. 80 2821-2827. 

Tani, T. Lakeman, C. D. E. Li, J.-F. Xu, Z. Payne, D. A. 1994. Crystallization behavior and improved properties for sol-gel derived PZT and PLZT thin layers processed with a lead oxide cover coating. Ceram. Trans. 43 89-106. 

C. M. Payne, C. Bernstein and H. Bernstein, Apoptosis overview emphasizing the role of oxidative stress, DNA damage and signal-transduction pathways, Leuk. Lymphoma, 1995, 19(1-2), 43. 

H. Bernstein, C. M. Payne, C. Bernstein, J. Schneider, S. E. Beard and C. L. Crowley, Activation of the promoters of genes associated with DNA damage, oxidative stress, ER stress and protein malfolding by the bile salt, deoxycholate, Toxicol. Lett., 1999, 108(1), 37. 

C. M. Payne, C. Weber, C. Crowley-Skillicorn, K. Dvorak, H. Bernstein, C. Bernstein, H. Holubec, B. Dvorakova and H. Garewal, Deoxycholate induces mitochondrial oxidative stress and activates NF-kappaB through multiple mechanisms in HCT-116 colon epithelial cells, Carcinogenesis, 2007, 28(1), 215. 

C. L. Crowley-Weber, K. Dvorakova, C. Crowley, H. Bernstein, C. Bernstein, H. Garewal and C. M. Payne, Nicotine increases oxidative stress, activates NF-kappaB and GRP78, induces apoptosis and sensitizes cells to genotoxic/xenobiotic stresses by a multiple stress inducer, deoxy-cholate relevance to colon carcinogenesis, Chem. Biol. Interact., 2003, 145(1), 53. 

Mauk, C.E. Prengle, H.W. Payne, N.E. Oxidation of Pesticides by Ozone and Ultraviolet Light Houston Research Inc. Houston, TX, 1976. 

Payne, T.E. Waite, T.D. (1991) Surface com-plexation modeling of uranium sorption data obtained by isotopic exchange techniques. Radiochim. Acta 52-53 (Pt 2) 487-493 Peacock, M.A. (1942) On goethite and lepidocro-cite. Trans. Roy. Soc. Ca. 36 107-119 Peacock, S. Rimmer, D.L. (2000) The suitability of an iron oxide-rich gypsum by-product as a soil amendment. J. Environ. Qual. 29 1969-1975... 

The native iron-sulfur clusters of many enzymes can be directly observed by EPR spectroscopy (Beinert, 1978). In several cases, appearance of the DNIC signal from nitrogen oxide-treated enzyme (Salerno et al., 1976 Dervartanian et al., 1973 Hyman et al., 1992) or cells (Reddy et al., 1983 Payne et al., 1990) results in the disappearance of these native signals, indicating conversion of the iron from the native cluster coordination to DNIC complexes. However, loss of EPR signal from native clusters does not necessarily correlate with appearance of the DNIC signal (Hyman et al., 1992). 

The pathway for the reduction of nitrate by denitrifiers is generally recognized to involve four steps as shown in Eq. (1) (Betlach and Tiedje, 1981 Braun and Zumft, 1991 Goretski and Hollocher, 1990 Knowles, 1982 Payne, 1981). The N-oxides represented. 

Balderston, W. L., Sherr, B., and Payne, W. J. (1976). Blockage by acetylene of nitrous oxide reduction in Pseudomonas perfectomarinus. Appl. Environ. Microbiol. 31, 504-508. 

Costa, C., Macedo, A., Moura, 1., Moura, j. j. G., LeGall, J., Berber, Y., Liu, M.-Y., and Payne, W. J. (1990). Regulation of the hexaheme nitrite/nitric oxide reductase of Desulfovibrio desulfuricans, Wohnella succinogenes, and Escherichia coli. A mass spectro-metric study. FEBS Lett. 276, 67-70. 

Payne, W. J., Grant, M. A., Shapleigh, J., and Hoffman, P. (1982). Nitrogen oxide reduction in Wolinella succinogenes and Campylobacter species. J. Bacterial. 152, 915-918. 

Shapleigh, j. P., and Payne, W. j. (1985b). Nitric oxide-dependent proton translocation in various denitrifiers. J. Bacterial. 163, 837-840. 

Shapleigh, J. P., Davies, K. J. P., and Payne, W. J. (1987). Detergent inhibition of nitric-oxide reductase activity. Biochim. Biophys. Acta 911, 334-340. 

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