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US5141860.Pdf |||||||||||||III USOO5141860A United States Patent (19) 11) Patent Number: 5,141,860 Bornemann et al. 45 Date of Patent: Aug. 25, 1992 (54) PREPARATION OF ACYLATED SUCROSE OERVATIVES OTHER PUBLICATIONS 75 Inventors: Stephen Bornemann, Leamington Pu, Chemical Abstracts, vol. 112(9), May 7, 1990, Spa; John M. Cassells, St. Ives; Clive #171972d. L. Combes, Reading, all of Great Bai et al., Biological Abstracts, vol. 88(3), 1989, #29969. Britain; Jonathan S. Dordik, Iowa Zheng et al., Chemical Abstracts, vol. 112(3), Jan. 15, City, Iowa; Andrew J. Hacking, 1990, #16029h. - Mortimer, Great Britain Zhang et al., Chemical Abstracts, vol. 95(9), Aug. 31, 1991, #73690x. 73) Assignee: Tate & Lyle Public Limited Company, Xia et al., Chemical Abstracts, vol. 113(25), Dec. 17, United Kingdom 1990, #224305t. (21) Appl. No.: 412,670 Hook Research Group, Biological Abstracts, vol. 79(9), 1985, #80151. 22 Filed: Sep. 26, 1989 Chang, Biological Abstracts, vol. 79(10), 1985, #89135. 30 Foreign Application Priority Data Li et al., Biological Abstracts, vol. 90(7), 1990, #79317. Kirchner et al., J. Am. Chem. Soc. (1985), vol. 107, pp. Sep. 27, 1988 GB United Kingdom ................. 882264 7072-7076. 51 int. Cl. ........................ C12P 19/12; C12P 19/44 Therisodet al., J. Am. Chem. Soc. (1986), vol. 108, pp. 52 U.S. Cl. .................................... 435/100; 435/198; 5638-5640. 435/72; 435/74 Zaks et al., Science (1984), vol. 224, pp. 1249-1251. 58) Field of Search .................... 435/100, 198, 72, 74 Primary Examiner-Ronald W. Griffin 56) References Cited Assistant Examiner-Pamela S. Webber U.S. PATENT DOCUMENTS Attorney, Agent, or Firm-Ostrolenk, Faber, Gerb & Soffen 3,767,526 10/1973 Suzuki et al. ....................... 435/208 4,002,609 1/1977 Khan ........................ ... 536/19 57 ABSTRACT 4,362,869 2/982 Jenner et al. ......... ... 536/122 Sucrose derivatives partially acylated in each ring can 4,751.294 6/1988 Jackson ............................... 536/22 be obtained by treating a fully or partially acylated FOREIGN PATENT DOCUMENTS sucrose derivative with an enzyme having sucrose es 357476 3/1990 European Pat. Off. ............ 435/100 terase activity capable of removing at least one acyl 1437048 5/1976 United Kingdom ... ... 536/15 group from each ring, generally comprising or being a 1492791 1 1/1977 United Kingdom ................ 536/122 component of a lipase, esterase, amylase, a-galactosi 1543163 3/1979 United Kingdom . dase or protease preparation, the enzyme treatment 2065648 7/1981 United Kingdom 536/15 being effected in an aqueous system. Sucralose can be 2079749 1/1982 United Kingdom .... ... 536/15 obtained by using this method to obtain a sucrose 2088855 6/1982 United Kingdom ... ... 536/22 2101989 1/1983 United Kingdom 536/115 2,3,6,3',4'-penta ester which can then be chlorinated and 2104063 3/1983 United Kingdom a - ... 53.6/122 de-esterfied. Some of the penta acetates, tetraacetates 2127807 4/1984 United Kingdom.... ... 536/122 and mixed acetates/butyrates are new compounds. 282039 5/1987 United Kingdom ... ... 536/122 2195632 4/1988 United Kingdom ................ 536/15 22 Claims, No Drawings 5,141,860 1. 2 Haines, Konowicz and Jones obtained the 2,3,4,6,1,6'- PREPARATION OF ACYLATED SUCROSE hexaacetate by storing SOA in n-propylamine at room DERVATIVES temperature for 50 minutes or in isopropylamine at room temperature for 72 hours (personal communica This invention relates to the preparation of partially tion). Thus, very few of the intermediates required for acylated derivatives of sucrose by the enzymatic deacy the production of sweet chlorosugars can be prepared lation of sucrose octaacylates, particularly sucrose oct by chemical deacylation of SOA. Acetyl groups can be aacetate (SOA), and to certain novel sucrose acylates removed from one ring of sucrose (6- or 6'-, or 4'-, or 1'- prepared by this process. and 3'-, or 3'- and 4'-) but not from both. Partially acylated sucrose derivatives are useful as O Another possibility is to achieve this specificity using intermediates in the preparation of other sucrose deriva enzymatic catalysis. Several groups of enzyme will tives such as esters and ethers, in which the required catalyse de-acylation reactions although all come in the substituents are at positions other than those protected general classification of hydrolytic enzymes. Esterases by the acyl groups. These include certain intensely predominantly hydrolyse glycerol esters, but will act on sweet derivatives of sucrose in which the hydroxy 15 a wide range of substrates. Lipases are a class of este groups at one or more of the 4-, 1'-, 4-, and 6'-positions rases which work at interfaces, which in nature usually are replaced by halogen atoms, as mentioned in British means membranes, but they will work at the interface of Patents No. 1,543,167; No. 2,088,855; No. 2,101,989; two immiscible liquids. Proteases will also hydrolyze No. 2,104,063 and No. 2,127,806. Of particular interest amongst these compounds is the high intensity sweet esters. There are several classes: serine, sulphydryl and ener sucralose, 4, 1,6'-trichloro-4, l',6'-trideoxygalac metaloproteinases, for example, all of which can show tosucrose. Other compounds of interest that can be de-esterification activity. As a sugar is being used in this prepared by means of the acylated intermediates in work, it may be speculated that carbohydrase enzymes clude sucrose benzoates, some of which posses useful which normally hydrolyze the bond between two sugar bittering properties. 25 moieties might hydrolyze a sugar ester. The synthesis of these compounds is complicated A further possibility is to combine chemical and enzy because of the selectivity that is required in the substitu matic methods to deacylate sucrose octaacylates pre tion of particular hydroxyl groups. It is necessary to pared by chemical deacylation may be further treated protect at least some of the hydroxyl groups that are to with an enzyme to effect hydrolysis of additional acyl be retained while some or all of the other hydroxyl 30 groups. groups are replaced with the desired substituents. Nearly all the published work in this areas has con One method of achieving this is described in British cerned the selective deacylation of monosaccharides. Patent No. 2,065,648B which relates to the preparation Thus, for example, H. M. Sweers and C-H Wong (JAm of sucralose. It involves reacting the 6-, 1'- and 6'-posi Chern Soc 1986, 108, 6421-6422) have reported the tions of sucrose with trityl chloride and reacting the 35 regioselective deacylation of methyl 2,3,4,6-tetra-O- remaining free hydroxyl groups with acetic anhydride, pentanoyl-D-hexopyranosides to give the 6-hydroxy followed by removing the trity groups. The acetate derivatives, using the lipase from Candida cylindracea. group at position 4 may be migrated to the 6- position The reaction was carried out in phosphate buffer (0.1M, and the resulting compound with only the 4, 1'- and pH 7) at ambient temperature, with stirring, over three 6'-hydroxyl groups free may be chlorinated and the days, the substrate being added as a solution in acetone. acetate groups removed to yield sucralose. Alterna Deacylation was specific to the 6-position. Acetyl de tively the greater reactivity of the 4-, 6-, 1'- and 6'- rivatives were not substrates for the enzyme. positions may be exploited. If one or more of these The only report known to us of enzymatic deacyla positions is protected then the remainder may be selec tion of an acylated disaccharide substrate was described tively chlorinated using milder reaction conditions, 45 by Kloosterman et al at a meeting in Stockholm in Au Thus in British Patents 2,079,749 and 2,195,632 the 6 gust 1988. They showed that wheat germ lipase (Sigma position is acetylated, the 4-, 1'- and 6'- positions are L-3001) under aqueous conditions removed three acetyl chlorinated and the acetate is removed to give su groups from sucrose octaacetate, all from the fructose cralose. ring; thus obtaining the l', 4', 6'-tri-hydroxy pentaace A strategy that has more general applicability and SO tate. could yield a range of halogenated sucrose derivatives There is thus a need for a method of removing se involves the selective removal of acyl groups from lected acyl groups from both rings of sucrose octaace octaacyl derivatives of sucrose. One such compound is tate (SOA). sucrose octaacetate which can be synthesized cheaply SOA is insoluble in water and therefore would not from sucrose and acetic anhydride and is available com 55 seen to be an easy subject for deacylation by enzymatic mercially. hydrolysis. However, we have found that certain lipase, Selective chemical de-esterification of SOA is limited protease and esterase enzymes can be used to deacylate to only a few positions. Thus Ballard, Hough and Rich SOA in certain organic solvents in the presence of wa ardson (Carbohydrate Research 24, 152, 1972 and 34, ter, generally 50% or more, or in aqueous dispersions of 184, 1974) obtained a mixture of hepta-O-acetyl su SOA. Further, these enzymes can be used to deacylate croses (OH 6 or 6' or 4) by deacylation of sucrose SOA selectively, at one or more of the 4-, 6-, 1-, 4' and octaacetate (SOA) in chloroform on an aluminum oxide 6'-positions, leaving at least the 2-, 3- and 3'-positions column. Later, Capek, Vydra, Ranny and Sedmera protected. (Collection Czechoslovak Chem. Commun. 50, 2191, Thus, according to the present invention we provide 1985) obtained in addition to the heptaacetates, two 65 a method for the preparation of tri-, tetra-, penta-, hexa hexaacetates (OH 1" and 3", OH 3' and 4) by deacetyla or heptaacylates of sucrose with acyl groups at least the tion of a methanolic solution of SOA on aluminum 2-, 3- and 3'-positions and, where there are two or more oxide impregnated by potassium carbonate.
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