Lactose: Chemical Derivatives

  • L. A. W. Thelwall


Lactose (4-O-β-d-galactopyranosyl-d-glucose) 1 is a naturally occurring carbohydrate found in the milk of most mammals. It is composed of d-galactose and d-glucose and is therefore termed a disaccharide. A number of disaccharides exist in nature, of which lactose is one of the most abundant. The individual components of a disaccharide may be joined to each other in a variety of ways. In lactose, the inter-sugar link is between the reducing (anomeric) centre of galactose and the C-4 hydroxyl group of glucose. This type of linkage results in a reducing disaccharide, as the glucose sugar in lactose has a potential aldehyde function. Sucrose, for example, is a non-reducing disaccharide as it is linked via the anomeric centres of its components, glucose and fructose.


Chemical Derivative Cerium Ammonium Nitrate Lactobionic Acid Cyclic Acetal Anomeric Centre 


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  1. Abbas, S.A. and Baer, H.H. (1979) Synthesis of O-β-L-fucopyranosyl-(1→3-O-β-D-galactopyranosyl-(1→ 4)-D-glucopyranose (3’-O-β-L-fucopyranosyllactose). Carbohydr. Res., 77, 117–29.Google Scholar
  2. Abbas, S.A. and Baer, H.H. (1980) Synthesis of O-a-L-fucopyranosyl-(1→3)-O-β-D-galactopyranosyl-(1→ 4)-D-glucose (3’-O-α-L-fucopyranosyllactose) and an improved route to its 13-(1“→3’)-linked isomer. Carbohydr. Res., 84, 53–60.Google Scholar
  3. Abbas, S., Dapgupta, F., Asa, D., et al. (1994) Preparation of substituted lactose derivatives as cell adhesion inhibitors. PCT Int. Appl. WO 94 00, 477.Google Scholar
  4. Adachi, T., Suyama, T., Kikuchi, E., et al. (1987) Manufacture of 6’-galactosyllactose by lactose assimilating microorganisms. Jap. Pat. JP 62 79, 791.Google Scholar
  5. Adelhorst, K. and Bock, K. (1992) The function of the 5-hydroxymethyl group of lactose in enzymic hydrolysis with ß-galactosidase from E. coli. Acta Chem. Scand., 46, 1114–21.Google Scholar
  6. Akiyama, T. (1991) Separation of neutral mono-and oligosaccharides derivatised with ethyl p-aminobenzoate by high-performance liquid chromatography on an amine-bonded vinyl alcohol copolymer column. J. Chromatogr., 588, 53–9.Google Scholar
  7. Akiyama, Y., Yoshihashi, S., Honda, T. and Sakauchi, I. (1988) Process for the continuous manufacture of lactulose from lactose. Jap. Pat. JP 63, 119, 492.Google Scholar
  8. Ali, M.A., Hough, L. and Richardson, A.C. (1991) Chemistry of maltose and lactose. Part 9. Thio and epidithio derivatives of methyl-β-lactoside. Carbohydr. Res., 216, 271–87.Google Scholar
  9. Alonso-Lopez, M., Bernabe, M., Fernandez-Mayoralas, A., et al. (1986) Chiral macrocyclic compounds from lactose derivatives. Carbohydr. Res., 150, 103–9.Google Scholar
  10. Alonso-Lopez, M., Barbat, J., Fanton, E., et al. (1987) The acetonation of lactose and benzyl ß-lactoside with 2-methoxypropene. Tetrahedron, 43, 1169–76.Google Scholar
  11. Alonso-Lopez, M., Martin-Lomas, M. and Penades, S. (1988) Chiral macrocycles incorporating lactitol and 4–0-(1-deoxy-D-galactitol-1-yl)-D-glucitol residues. Carbohydr. Res., 175, 133–6.Google Scholar
  12. Breg, J., Romijn, D., van Halbeek, H., et al. (1988) Characterisation of four lactose monophosphates by application of phosphorus-31, carbon-13 and proton NMR spectroscopy. Carbohydr. Res., 174, 23–36.Google Scholar
  13. Carobbi, R. and Innocenti, F. (1989) Process for preparing lactulose from lactose by epimerisation with sodium aluminate. Eur. Pat Appl. EP 320, 670.Google Scholar
  14. Christiansen-Brams, I., Meldal, M. and Bock, K. (1992) Synthesis of the 1amino-alditols derived from cellobiose, lactose and maltose. A comprehensive NMR study of some alditols and amino-alditols. J. Carbohydr. Chem., 11, 8 1335.Google Scholar
  15. D’Accorso, N.B., Zuazo, B.N. and Thiel, I.M.E. (1988) Synthesis and spectra of some octa-O-benzoyl aldobiononitriles. Carbohydr. Res., 172, 147–55.Google Scholar
  16. De Haar, W.T. and Pluim, H. (1988) Preparation and decolorisation of lactulose. Eur. Pat. Appl. EP 339, 749.Google Scholar
  17. Defaye, J., Gadelle, A. and Pederson, C. (1991) Method of preparation of 1alkylthioglycosides and alkylglycosides, anomer mixtures obtained by this process, and their use as nonionic detergents. Eur. Pat. Appl. EP 411, 980.Google Scholar
  18. Dendene, K., Guihard, L., Nicolas, S. and Bariou, B. (1994) Kinetics of lactose isomerisation to lactulose in an alkaline medium. J. Chem. Technol. Biotechnol., 61, 37–42.Google Scholar
  19. Deya, E. Takahashi, K. and Ikeuchi, Y. (1990) Production of high-purity lactulose syrup. Eur. Pat. Appl. EP 357, 068.Google Scholar
  20. Deya, E., Yanahira, S., Aboko, K. and Kikuchi, E. (1987) Cattle feed containing galactooligosaccharides for prevention of diarrhea. Fr. Demande FR 2, 591, 484.Google Scholar
  21. Dorscheid, M. and Krumbholz, R. (1990) Preparation of lactulose by isomerisation of lactose in the presence of borax. Eur. Pat. Appl. EP 375, 046.Google Scholar
  22. Dowd, M.M., Baynes, J.W. and Thorpe, S.R. (1992) Synthesis of N,N-dilactitol ethylenediamine: a versatile spacer for attachment of residualizing labels to protein. Anal. Biochem., 205, 369–71.Google Scholar
  23. Egli, H. (1988) Computer-aided evaluation of two-dimensional multiple quantum carbon shift correlation. Magn. Reson. Chem., 26, 876–80.Google Scholar
  24. Fazekas, J., Farkas, I (Mrs)., Farkas, I., et al. (1985) IV-O-β-D-galactopyranosyl-Dfructofuranose for pharmaceutical use. Hungarian Pat. HU 35, 267.Google Scholar
  25. Fernandez, P. and Jimenez-Barbero, J. (1994) The conformation of some halodeoxy analogs of methyl 3-lactoside in D20 and DMSO-d6 solutions. J. Carbohydr. Chem., 13, 207–33.Google Scholar
  26. Fernandez, P., Jimenez-Barbero, J. and Martin-Lomas, M. (1994) Syntheses of all the possible monomethyl ethers and several deoxyhalo analogs of methyl (3lactoside as ligands for the Ricinus communis lectins. Carbohydr. Res., 254, 61–79.Google Scholar
  27. Fernandez-Mayoralas, A. and Martin-Lomas, M. (1985) IV-O-β-D-Galactopyranosyl-3-O-methyl-D-glucose: a new synthesis and application to the evaluation of intestinal lactase. Carbohydr. Res., 140, 81–91.Google Scholar
  28. Fillippini, A. (1985) Lactulose purification. Eur. Pat. Appl. EP 158, 148.Google Scholar
  29. Fu, W. and Song, K. (1993) Removal of boric acid catalyst in lactose isomerisation. Chinese Pat. CN 1073, 668.Google Scholar
  30. Fuesgen, I. and Schumann, C. (1984) Lactulose, classical indications and potential uses. Pharm. Ztg., 139(15), 9–12, 14, 16–17.Google Scholar
  31. Goux, W.J. (1988) The determination of complex carbohydrate structure by using carbonyl carbon resonances of peracetylated derivatives. Carbohydr. Res., 184, 47–65.Google Scholar
  32. Greig, B.D. and Payne, G.A. (1985) Epimerisation of lactose to free lactulose in model milk solutions. J. Dairy Chem., 52, 409–17.Google Scholar
  33. Handa, Y. and Nakamura, S. (1989) Saccharide fatty acid ester pharmaceutical compositions for the treatment of skin wounds. Eur. Pat. Appl. EP 343, 671.Google Scholar
  34. Harper, W.J. (1992) Lactose and lactose derivatives, in Whey Lactose Process, ( J. Zadow and J. Greig eds.) Elsevier Applied Science Publishers, London, pp. 317–60.Google Scholar
  35. Hasegawa, M. and Muroki, H. (1988a) A process for preparation of sugar ethers useful as surfactants in pharmaceuticals and cosmetics, Jap. Pat JP 63 35, 590.Google Scholar
  36. Hasegawa, M. and Muroki, H. (1988b) Cosmetics containing hydroxyalkyl sugar ethers. Jap. Pat. JP 63, 222, 106.Google Scholar
  37. Hatakeyama, M., Kinomura, K. and Sakakikibara, T. (1987) Peracetylation of monosaccharides and oligosaccharides. Jpn. Kokai Tokky Koho JP 62 42, 996.Google Scholar
  38. Hattori, T. (1991) Enzymic manufacture of glycosides. Jap. Pat. JP, 03, 236, 788.Google Scholar
  39. Hendriks, H.E.J. (1993) Selective catalytic oxidations of lactose and related carbohydrates. Gov. Rep. Announce. Index (US), 93(8), Abstr. No. 321, 567.Google Scholar
  40. Hicks, K.B. and Parrish, F.W. (1980) A new method for the preparation of lactulose from lactose. Carbohydr. Res., 82, 393–97.Google Scholar
  41. Hough, L., Richardson, A.C. and Thelwall, L.A.W. (1979) Reaction of lactose with 2,2-dimethoxypropane: a tetra-acetal of novel structure. Carbohydr. Res., 75, C11 - C12.Google Scholar
  42. Huh, K.T., Toba, T. and Adachi, S. (1991) Oligosaccharide structures formed during acid hydrolysis of lactose. Food Chem., 39, 39–49.Google Scholar
  43. Ikeda, I. and Klibanov, A.M. (1993) Lipase-catalysed acylation of sugars solubilised in hydrophobic solvents by complexation. Biotechnol. Bioeng., 42, 788–91.Google Scholar
  44. Ishikawa, S., Nishida, M., Ukiya, C. and Kanao, H. (1992) Detergent compositions with good resistance to skin irritation, Jap. Pat. JP 04, 332, 795.Google Scholar
  45. Itoh, T. (1989) Physical properties of lactose. Rakuno Kagaku, Shokuhin no Kenkyu, 38, A247–52.Google Scholar
  46. Jain, R.K., Locke, R.D. and Matta, K.L. (1991) Synthetic studies in carbohydrates. Part LXXVII. A convenient synthesis of O-a-L-fucopyranosyl-(→2)-O41D-galactopyranosyl-(1 →4)-D-glucopyranose (2’-O-a-L-fucopyranosyl lactose). Carbohydr, Res., 212, Cl-3.Google Scholar
  47. Johnson, T. and Rennie, R.A.C. (1992) Saccharide mercaptals. Eur. Pat. Appl. EP 516, 300.Google Scholar
  48. Kallin, E. and Loenn, H. (1986) New derivatisation and separation procedures for reducing oligosaccharides. Glycoconjugate J., 3, 311–19.Google Scholar
  49. Kallin, E., Loenn, H. and Norberg, T. (1988) Derivatisation procedures for reducing oligosaccharides. Part 2: Chemical transformations of 1-deoxy-1-(4trifluroroacetamidophenyl) aminoalditols. Glycoconjugate J., 5, 145–50.Google Scholar
  50. Kallin, E., Loenn, H., Norberg, T. and Elofsson, M. (1989) Derivatisation procedure for reducing oligosaccharides. Part 3. Preparation of oligosaccharide glycosylamines, and their conversion into oligosaccharide-acrylamide copolymers. Carbohydr. Res., 8, 597–611.Google Scholar
  51. Kamath, P.V., Ismail, J., Ahmed, M.F., et al. (1993) Stabilisation of a-nickel hydroxide in the presence of organic additives: chemical route to bulk synthesis. J. Mater. Chem., 3, 1285–7.Google Scholar
  52. Kartha, K.P.R. and Jennings, H.J. (1990) A simplified one-pot preparation of acetobromo sugars from reducing sugars. J. Carbohydr. Chem., 9, 777–81.Google Scholar
  53. Katta, Y., Ohkuma, K., Satouchi, M. and Takahashi, R. (1991) Method of preparing galacto-oligosaccharides. Eur. Pat Appl. EP 435, 657.Google Scholar
  54. Kawashima, S., Ide, H., Kato, K., et al. (1990) Manufacture of lactitol anhydrate crystals and crystal compositions containing lactitol anhydrate. Jap. Pat. JP 02, 255, 694.Google Scholar
  55. Kikuchi, K. and Sugiyama, H. (1988) Enzymic esterification of lactose with fatty acids. Jap. Pat. JP, 63, 222, 697.Google Scholar
  56. Kinzy, W. (1992) Method for the preparation of sugar epitopes. Eur. Pat. Appl. EP 518, 270.Google Scholar
  57. Kirst, E., Lipke, B. and Westphal, G. (1990) Industrial significance of lactose. Part 2. Utilisation of lactose. Milforsch. Milprax. 32, 42–4.Google Scholar
  58. Kishimoto, M., Konishi, S. and Bito, M. (1993) Preparation of water-soluble tetraphenylporphin glycosides. Jap. Pat. JP 05, 112, 593.Google Scholar
  59. Koketsu, N. and Hiei, T. (1992) Preparation of lactitol trihydrate crystals and compositions containing the crystals. Jap. Pat. JP 04 13, 686.Google Scholar
  60. Kovacs, A., Szurmai, Z., Janossy, L., et al. (1990) Preparation of arylamino sugars. PCT Int. Appl. WO 90 04, 600.Google Scholar
  61. Kozempel, M. and Kurantz, M. (1994a) A continuous reactor system for production of lactulose. J. Chem. Technol. Biotechnol., 59, 265–9.Google Scholar
  62. Kozempel, M. and Kurantz, M. (1994b) The isomerisation kinetics of lactose to lactulose in the presence of borate. J. Chem. Technol. Biotechnol., 59, 25–9.Google Scholar
  63. Lalezari, I. (1991) Polyol polyester preparation in aqueous media using mixed anhydrides and use of the polyesters as fat substitutes in food and in cosmetics. PCT Int. Appl. WO 91 01, 322.Google Scholar
  64. Langlois, V. and Williams, J.M. (1994) Carbohydrate derived surfactants: synthesis and phase behaviour of methyl 4’,6’-di-O-alkyl-3-lactosides. J. Chem. Soc. Perkins Trans. J, 15, 2103–6.Google Scholar
  65. Latge, P., Bon, M., Rico, I. and Lattes, A. (1992) Complete proton and carbon-13 NMR analysis (1D and 2D) of long-chain N-alkyl lactosylamines. N. J. Chem., 16, 387–93.Google Scholar
  66. Lee, Y.C., Honda, S. and Kakehi, K. (1992) Method for labelling sugars. Eur. Pat. Appl. EP 480, 751.Google Scholar
  67. Lehmann, J. and Neumann, B. (1990) Reactive pseudooligosaccharides as potential irreversible inhibitors for sugar-binding proteins: synthesis of the diastereoisomers of (3,4,6/5)-3,4-epoxy-6-(ß-D-galactopyranosylthio)-5-hydroxycyclohexene. Carbohydr. Res., 200, 355–61.Google Scholar
  68. Lichtenthaler, F.W., Kaji, E. and Weprek, S. (1985) Disaccharide derived 2-oxoand 2-oximinoglycosyl bromides: novel, conveniently accessible building blocks for the expedient construction of oligosaccharides with a-D-glucosamine, ß-Dmannose and ß-D-mannosamine as constituent sugars. J. Org. Chem., 50, 350–515.Google Scholar
  69. Linko, P. (1982) Lactose and lactitol, in Nutritive Sweeteners, ( G. Birch and K.J. Parker eds.) Applied Science Publishers, London, pp. 109–31.Google Scholar
  70. Linko, P., Saijonmaa, T., Heikonen, M. and Kreula, M. (1980) Lactitol, in Carbohydrate Sweeteners in Food and Nutrition, (P. Koivistoinen and L. Hyvönen eds.) Academic Press, London, pp. 243–57.Google Scholar
  71. Maranduba, A. and Veyrieres, A. (1985) Glycosylation of lactose. Synthesis of methyl O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1→3)-O-β-D-galactopyranosyl-(1→4)-β-D-glucopyranoside and methyl O-β-D-galactopyranosyl-(1→4)-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1–43)-O-β-D-galactopyranosyl-(1→4)-3-D-glucopyranoside. Carbohydr. Res., 135, 330–36.Google Scholar
  72. Matsumoto, K., Ito, M. and Kudo, S. (1992) Feed containing galactosyl diasaccharides for domestic animals. Jap Pat. JP 04, 360, 652.Google Scholar
  73. Matsumura, S. and Mizuno, H. (1992) Preparation of cœ-hydroxyalkyl 13-galactosides as non-ionic surfactants. Jap. Pat. JP 04, 149, 190.Google Scholar
  74. Matsumura, S., Kubokawa, H. and Yoshikawa, S. (1991) Enzymic synthesis of whydroxyalkyl-and n-alkyl-β-D-galactopyranosides by the transglycosylation reaction of ß-galactosidase. Chem. Lett., 6, 945–8.Google Scholar
  75. Matsuo, K. and Hasuike, Y. (1990) Synthesis of (—)-frontalin starting from D-lactose. Yagugaku Zasshi, 110, 555–60.Google Scholar
  76. Mbabazi, J. (1985) Sugar complexes of tin(IV), antimony(V), and tellurium(VI) hydroxyanions. Carbohydr. Res., 140, 151–4.Google Scholar
  77. Mentech, J., Beck, R. and Burzio, F. (1993) Preparation of partially acylated carbohydrates. PCT Int. Appl. WO 93 01, 200.Google Scholar
  78. Meyer, R.S., Root, J.M., Campbell, M.L. and Winter, D.B. (1989) Low calorie alkyl glycoside fatty acid polyester fat substitute. U.S. Pat. US 4, 840, 815.Google Scholar
  79. Meyer, R.S., Akoh, C.C., Swanson, B.G., et al. (1991) Polysaccharide fatty acid polyester fat substitute. U.S. Pat. US 4, 973, 489.Google Scholar
  80. Miayake, H., Kurahashi, M., Toda, H., et al. (1991) Enzymic process for producing saccharide fatty acid monoesters. Eur. Pat. Appl. EP 413, 307.Google Scholar
  81. Miyaji, H., Kitaguni, H., Hirota, S. and Kikuchi, H. (1987) Preparation of higher aliphatic acid derivatives of lactosylamine useful in drug delivery systems such as liposomes. Jap. Pat. JP 62, 209, 092.Google Scholar
  82. Mizota, T. (1994) Lactulose and its physiological aspects. Rakuno Kagaku, Shokhin no Kenkyu, 43 (2), A35–41.Google Scholar
  83. Montoro, F., Calatayud, J. and Luna, M. (1985) Lactose sulphate derivative. Spanish Pat. ES 532, 088.Google Scholar
  84. Morikawa, A. and Kuzuhara, H. (1990) Novel partial protection of 1,6-anhydroß-lactose. J. Carbohydr. Chem., 9 (2–3), 167–79.Google Scholar
  85. Murakami, K., Maruyama, K. and Nagai, K. (1993) Jet-printing inks containing sugars or their fatty acid esters. Jap. Pat. JP 05 70, 722.Google Scholar
  86. Nagendra, R. and Rao, S.V. (1992) An improved colorimetric method for the estimation of lactulose in lactose-lactulose mixtures. Food Chem., 43, 399–402.Google Scholar
  87. Nagy L., Burger, K., Kurti, J., et al. (1987) Iron (III) complexes of sugar type ligands. Magy. Kern. Foly. 93; 289–93.Google Scholar
  88. Nishimura, S., Murayama, S., Kurita, K. and Kuzuhara, H. (1992) Novel 1,6anhydro-β-lactose derivatives for rapid and efficient syntheses of oligosaccharides sequences containing N-acetyl-lactosamine. Chem. Lett., 8, 1413–16.Google Scholar
  89. Olano, A. (1986) Lactose transformations of industrial significance. Alimentaria (Madrid), 23(172), 17, 19–22.Google Scholar
  90. Olano, A. and Martinez-Castro, L. (1989) Modification and Interactions of Lactose. Bulletin 238, International Diary Federation, Brussels, pp. 35–44.Google Scholar
  91. Olano, A., Lopez-Covarrubias, S.J., Ramos, M. and Suarez, J.A. (1986) The use of lactulose in the manufacture of low-lactose yogurt. Biotechnol. Lett., 8, 451–52.Google Scholar
  92. Ortiz Mellet, C., Menez Blanco, J.L., Garcia Fernandez, J.M. and Fuentes, J. (1993) Building blocks for glycopeptide synthesis. Disaccharide glycosyl isothiocyanates. J. Carbohydr. Chem., 12, 487–505.Google Scholar
  93. Paulsen, H. and Paal, M. (1985) Synthons of oligosaccharides. LIX. Synthesis of tetra-and trisaccharide sequences of asialo-GM1 and -GM2. Steering of regio-selectivity of glycosidation of lactoses. Carbohydr. Res., 137, 39–62.Google Scholar
  94. Platzer, N., Davoust, D., Lhermitte, M., et al. (1989) Structural analysis of five lactose-containing oligosaccharides by improved high-resolution, two-dimensional proton NMR spectroscopy. Carbohydr. Res., 191, 191–207.Google Scholar
  95. Pojer, P., Montgomery, K.C., Hunyh, C.P. and Milligan, B. (1992) Esters of polyols and polycarboxylic acids and their preparation and use with metal salts for tanning. PCT Int. Appl. WO 92 18, 457.Google Scholar
  96. Porro, D., Mazzucotelli, L. and Ranzi, B.M. (1993) The lactose problem: traditional and advanced recovery. Ann. Microbiol. Enzimol., 43, 245–60.Google Scholar
  97. Pritzwald-Stegmann, B.F. (1986) Lactose and some of its derivatives. J. Soc. Dairy Technol. 39, 91–7.Google Scholar
  98. Purokoski, S., Lajunen, K. and Hakkinen, P. (1987) A potentiometric study on the complex formation of arsenious acid, arsenite ion, telluric acid and tellurate ion with sugar acids and disaccharides in aqueous solution. Finn. Chem. Lett. 14, 1–5.Google Scholar
  99. Roeger, H., Pukr, H. and Kunz, M. (1990) Investigation on oxidative cleavage of reducing disaccharides. Zuckerindustrie (Berlin), 115, 174–81.Google Scholar
  100. Roelfsema, W.A. and Kuster, B.F.M. (1988) Prospects in the chemical derivatisation of lactose. Neth. Milk Dairy J., 42, 469–83.Google Scholar
  101. Rudzik, L. (1985) Infrared spectroscopic behaviour of lactose in aqueous solutions. Z. Lebensm.-Unters. Forsch., 180, 303–5.Google Scholar
  102. Ryabtseva, S.A., Rokhmistrov, V.V. and Miroshnichenko, V.I. (1992) Peculiarities of lactose isomerisation to lactulose in raw lactose solutions. Izv. Vyssb. Uchebn. Zaved., Pisch. Tekhnol., 1, 13–4.Google Scholar
  103. Saito, M. (1985) History of lactulose. Chiryogaku, 14, 629–32.Google Scholar
  104. Sato, K., Oku, K., Yoneyama, M. and Tsujisaka, Y. (1993) Glucosyl lactoside synthesised by the intermolecular transglucosylation using a-glucosidase. Denpun Kagaku, 40, 391–6.Google Scholar
  105. Schneller, M. and Geiger, R. (1992) Coupling of carbohydrates to (protein) carriers via amine-and thiol-containing compounds. Ger. Offen. DE 4, 101, 394.Google Scholar
  106. Singh, K., Fernandez-Mayoralas, A. and Martin-Lomas, M. (1994) Synthesis of oligosaccharides structurally related to E-selectin ligands. J. Chem. Soc., Chem. Commun., 6, 775–6.Google Scholar
  107. Sinkeldam, E.J., Woutersen, R.A., Hollanders, V.M.H., et al. (1992) Subchronic and chronic toxicity/carcinogenicity feeding studies with lactitol in rats. J. Am. Coll. Toxicol., 11, 165–88.Google Scholar
  108. Skibida, I.P., Sakharov, Andrei M. and Sakharov, A.M. (1993) Environmentally-safe oxidation process for the production of oxyacids from carbohydrates. Eur. Pat. Appl. EP 548, 399.Google Scholar
  109. So, R.S.C. and Willi, A.A. (1986) Carbonation agent. Eur. Pat. Appl. EP 185, 196.Google Scholar
  110. Suyama, K, Ogawa, K. and Adachi, S. (1987) Lactosan: 4-O-β-D-galactopyranosy1–1,6-anhydro-β-D-glucopyranose formation by heat treatment of lactose in vacuo. Food Chem., 24, 263–9.Google Scholar
  111. Swdeo, R., Arena, B.J. and Firth, B.E. (1989) Solid catalysts for epimerisation of aldoses; continuous interconversion of epimeric sugars. U.S. Pat. US 4, 815, 445.Google Scholar
  112. Takayanagi, T. (1989) Application of sugar esters to candies. New Food Ind., 31 (3), 33–9.Google Scholar
  113. Takei, T., Tanase, T., Yano, S. and Hidai, M. (1991) C-2 Epimerisation of disaccharides by calcium(II)-monoamine systems. A direct synthesis of (1–4)-linked disaccharides having a D-mannose unit as a reducing terminal. Chem. Lett., 9, 1629–32.Google Scholar
  114. Tanase, T., Nouchi, R., Oka, Y., et al. (1993) Synthesis and characterisation of nickel(II) complexes containing ligands derived from disaccharides and 1,3diaminopropane. J. Chem. Soc., Dalton Trans., 17, 2645–52.Google Scholar
  115. Tejima, S. and Chiba, T. (1984) Recent aspects of the chemistry of lactose and approaches to the synthesis of oligosaccharides and their analogs in human milk Seikagaku, 56, 467–78.Google Scholar
  116. Tejima, S. and Ishihara, H. (1984) Syntheses of constituent mono-and oligosaccharides in asparagine-linked glycan of glycoprotein. Yuki Gosei Kaguku Kyokaishi, 42, 552–6.Google Scholar
  117. Thelwall, L.A.W. (1980) Lactose, in Developments in Food Carbohydrate - 2, ( C.K. Lee ed.) Applied Science Publishers, London, pp. 275–326.Google Scholar
  118. Thelwall, L.A.W. (1982a) An Investigation of the Chemistry of Lactose, PhD Thesis, University of London, pp. 219.Google Scholar
  119. Thelwall, L.A.W. (1982b) Recent aspects of the chemistry of lactose. J. Dairy Res., 49, 713–24.Google Scholar
  120. Thelwall, L.A.W. (1985) Developments in the chemistry and chemical modification of lactose, in Developments in Dairy Chemistry - 3, ( P.F. Fox ed.) Elsevier Applied Science, London, pp. 35–67.Google Scholar
  121. Thelwall, L.A.W. (1987) Derivatives of lactose and their applications in food products, in Milk: Vital Force, Proc. 22nd Int. Dairy Congr., (The Hague) D. Reidel Publishing Co., Holland, pp. 749–58.Google Scholar
  122. Thornthwaite, D.W. (1993) Preparation of sugar esters useful as peroxy acid bleach precursors. Eur. Pat. Appl. EP 540, 279.Google Scholar
  123. Tomasik, P. and Zawadski, W. (1991a) A method for production of an aromatic essence with a fruity almond odour. Polish Pat. PL 154, 536.Google Scholar
  124. Tomasik, P. and Zawadski, W. (1991b) A method for production of the aromatic essence of maple syrup. Polish Pat. PL 154, 215.Google Scholar
  125. Tomasik, P. and Zawadski, W. (1991c) A method for production of the aromatic essence of almond. Polish Pat. PL 154, 216.Google Scholar
  126. Tomaskik, P. and Zawadski, W. (1991d) A method for production of the aromatic essence of prunes. Polish Pat. PL 154, 534.Google Scholar
  127. Toyoda, T. and Yasuda, K. (1990) Galactosyllactitol and its manufacture with galactosidase. Jap. Pat. JP 02, 283, 291.Google Scholar
  128. Tsukagoshi, K. and Shinkai, S. (1991) Specific complexation with mono-and disaccharides that can be detected by circular dichroism. J. Org. Chem., 56, 4089–91.Google Scholar
  129. Tsuru, M., Tamura, K., Takeda, M., et al. (1994a) Sweeteners for chewing gum. Jap. Pat. JP 06, 133, 696.Google Scholar
  130. Tsuru, M. Tamura, K., Takeda, M. et al. (1994b) Sweeteners for chewing gum. Jap. Pat. JP 06, 133, 697.Google Scholar
  131. Tsuru, M. Tamura, K., Takeda, M. et al. (1994c) Sweeteners for chewing gum. Jap. Pat. JP 06, 133, 698.Google Scholar
  132. Usui, Y., Sakai, K., Nanjo, F. and Katsumi, R. (1991) Preparation of oligosaccharides containing mannose. Jap. Pat. JP 03, 157, 391.Google Scholar
  133. Vasilisin, S.V., Khramtsova, R.F., Rokhmistrov, V.V., et al. (1988) Method of producing lactose-lactulose syrup. USSR Pat. SU 1, 392, 104.Google Scholar
  134. Verchere, J. and Hlaibi, M. (1987) Stability constants of borate complexes of oligosaccharides. Polyhedron, 6, 1415–20.Google Scholar
  135. Visser, R.A., van den Bos, M.J. and Ferguson, W.P. (1988) Lactose and Its Chemical Derivatives. Bulletin 233, International Dairy Federation, Brussels, pp. 33–44.Google Scholar
  136. Viswanathan, T. (1988) Ammonia-modified polyether polyols for use in polyurethanes. U.S. Pat. US 4, 734, 442.Google Scholar
  137. Warren, L. (1994) Bound Carbohydrates in Nature, Cambridge University Press, pp. 1–101.Google Scholar
  138. Weng, S., Chen, R. and Gu, T. (1990) Targeting effect of lactose-polylysine. Shengwu Huaxue Yu Shenhwu Wuli Xuebao, 22, 79–81.Google Scholar
  139. Winter, D., Meyer, R.S., Root, J.M. and Campbell, M.L. (1990) Alkyl glycoside fatty acid polyesters as fat substitutes. U.S. Pat. US 4, 942, 054.Google Scholar
  140. Wiwala, T., Klauze, M., Majer, Z. and Ostapuczuk, J. (1992) Preparation of saccharose, lactose and maltose polysulfate compounds with aluminium. Polish Pat. PL 158, 582.Google Scholar
  141. Wolowiec, S. and Drabent, K. (1985a) Polymeric iron(III)-sugar complexes. Proc.Sch.-Symp. Inorg. Biochem. Mol. Biophys., 241–2.Google Scholar
  142. Wolowiec, S. and Drabent, K. (1985b) Moessbaur study of iron(III)-reducing sugar complexes. J. Radioanal. Nucl. Chem., 95, 1–11.Google Scholar
  143. Yabushita, Y. and Takagi, K. (1987) High calorie intravenous nutrient containing water-soluble fatty acid esters of carbohydrates. U.S. Pat. US 4, 696, 916.Google Scholar
  144. Yano, S., Tanase, T., Takizawa, S. and Komiyama, S. (1988) A process for epimerisation of carbohydrates with metal salts and amines or their derivatives in lower alcohols. Jap. Pat. JP 63, 162, 698.Google Scholar
  145. Yokosuka, M., Nakazawa, Y., Tokumoto, T. and Tsumadori, M. (1993) Insecticides containing foam-producing surfactants, Jap. Pat. JP 05, 221, 804.Google Scholar
  146. Yoshino, T., Reuter, G., Kelm, S. and Schauer, R. (1986) Facile synthesis of 2’-substituted lactoses. Glycoconjugate J., 3, 7–14.Google Scholar
  147. Yuasa, H., Hindsgaul, O. and Palcic, M.M. (1992) Chemical-enzymic synthesis of 5’-thio-N-acetyllactosamine: the first disaccharide with sulphur in the ring of the non-reducing sugar. J. Am. Chem. Soc., 114, 5891–2.Google Scholar
  148. Yukimura, I. and Kono, T. (1993) Galacto-oligosaccharides-containing feeds for livestock. Jap. Pat. JP 05, 219, 897.Google Scholar
  149. Zadow, J.G. (1984) Lactose: properties and uses. J. Dairy Sci., 67, 2654–79.Google Scholar
  150. Zadow, J.G. (1987) The use of lactose in food products, in Milk: Vital Force, Proc. Int. 22nd Dairy Congr. (The Hague), D. Reidel Publishing Co., Holland, pp. 737–48.Google Scholar
  151. Zhou, Z., Ogden, S. and Leary, J.A. (1990) Linkage position determination in oligosaccharides: mass spec. study of lithium-catonized carbohydrates. J. Org. Chem. 55, 5444–6.Google Scholar

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© Springer Science+Business Media Dordrecht 1997

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  • L. A. W. Thelwall

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