The reactions of 3-deoxy-d-manno-oct-2-ulosonic acid (KDO) in dilute acid
作者： Paul A. McNicholas , Michael Batley , John W. Redmond
DOI: 10.1016/0008-6215(87)80073-3
关键词: Semicarbazide 、 3-Deoxy-D-manno-oct-2-ulosonic acid 、 Chemistry 、 Stereochemistry 、 Dilute acid 、 Organic chemistry 、 Analytical chemistry 、 Biochemistry 、 General Medicine
摘要: Abstract On heating in dilute acid, 3-deoxy- d -manno-oct-2-ulosonic acid (KDO) is converted into 2,7-anhydro-3-deoxy-α- -manno-2-octulofuranosonic and 5-( -erythro-1,2,3-trihydropropyl)-2-furoic acid. The former unreactive to periodic acid-thiobarbituric semicarbazide, its formation explains the depressed estimates of KDO lipopolysaccharides. Formation furoic can lead high using semicarbazide assay. Neither product be formed from 5-O-glycosyl-KDO.
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sci-hub.se 参考文章(20)
Miloslav Černý, Jan Staněk, 1,6-Anhydro Derivatives of Aldohexoses Advances in Carbohydrate Chemistry and Biochemistry. ,vol. 34, pp. 23- 177 ,(1977) , 10.1016/S0065-2318(08)60324-8
Wesley A. Volk, Nancy L. Salomonsky, Donald Hunt, Xanthomonas sinensis Cell Wall Lipopolysaccharide Journal of Biological Chemistry. ,vol. 247, pp. 3881- 3887 ,(1972) , 10.1016/S0021-9258(19)45117-X
L Skoza, S Mohos, Stable thiobarbituric acid chromophore with dimethyl sulphoxide. Application to sialic acid assay in analytical de-O-acetylation Biochemical Journal. ,vol. 159, pp. 457- 462 ,(1976) , 10.1042/BJ1590457
Frank M. Unger, The Chemistry and Biological Significance of 3-Deoxy-d-manno-2-Octulosonic Acid (KDO) Advances in Carbohydrate Chemistry and Biochemistry Volume 38. ,vol. 38, pp. 323- 388 ,(1981) , 10.1016/S0065-2318(08)60313-3
Stephen J. Angyal, The composition of reducing sugars in solution Advances in Carbohydrate Chemistry and Biochemistry. ,vol. 42, pp. 15- 68 ,(1984) , 10.1016/S0065-2318(08)60122-5
H Brade, Occurrence of 2-keto-deoxyoctonic acid 5-phosphate in lipopolysaccharides of Vibrio cholerae Ogawa and Inaba. Journal of Bacteriology. ,vol. 161, pp. 795- 798 ,(1985) , 10.1128/JB.161.2.795-798.1985
Deveshwari P. Khare, Anakshi Khare, Maheshwari P. Khare, Structure of “sugar T” Carbohydrate Research. ,vol. 81, pp. 285- 294 ,(1980) , 10.1016/S0008-6215(00)85659-1
Michel. DuBois, K. A. Gilles, J. K. Hamilton, P. A. Rebers, Fred. Smith, Colorimetric Method for Determination of Sugars and Related Substances Analytical Chemistry. ,vol. 28, pp. 350- 356 ,(1956) , 10.1021/AC60111A017
Ad Bax, Gareth A Morris, An improved method for heteronuclear chemical shift correlation by two-dimensional NMR Journal of Magnetic Resonance. ,vol. 42, pp. 501- 505 ,(1981) , 10.1016/0022-2364(81)90272-9
Paul A. McNicholas, Michael Batley, John W. Redmond, Synthesis of methyl pyranosides and furanosides of 3-deoxy-d-manno-oct-2-ulosonic acid (KDO) by acid-catalysed solvolysis of the acetylated derivatives Carbohydrate Research. ,vol. 146, pp. 219- 231 ,(1986) , 10.1016/0008-6215(86)85041-8