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United States Patent (19) 11) Patent Number: 4,505,757 Kojima Et Al

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United States Patent (19) 11) Patent Number: 4,505,757 Kojima Et Al United States Patent (19) 11) Patent Number: 4,505,757 Kojima et al. 45) Date of Patent: Mar. 19, 1985 54 METHOD FOR A SPECIFIC (56) References Cited DEPOLYMERIZATION OF A POLYSACCHARIDE HAVING AROD-LIKE U.S. PATENT DOCUMENTS HELICAL CONFORMATION 4,098,661 7/1978 Kikumoto et al. .............. 204/158 S 4,115,146 9/1978 Saint-Lebe et al. .................. 127/38 4,143,201 3/1979 Miyashiro et al. ... ... 536/102 75 Inventors: Takemasa Kojima, Yokohama; Kengo 4,155,884 5/1979 Hughes ..... ... 536/102 Tabata; Toshio Yanaki, both of Kobe; Mitsuaki Mitani, Sagamihara, all of 4,342,603 8/1982 Daniels .................................. 127/58 Japan FOREIGN PATENT DOCUMENTS 0008241 2/1980 European Pat. Off. ............ 536/102 73) Assignees: Kaken Pharmaceutical Co. Ltd.; Taito 52-21064 6/1977 Japan ..................................... 127/38 Co., Ltd., both of Tokyo, Japan Primary Examiner-Peter Hruskoci Attorney, Agent, or Firm-Oblon, Fisher, Spivak, 21 Appl. No.: 460,300 McClelland & Maier 22 Filed: Jan. 24, 1983 57 ABSTRACT The description describes a process for depolymeriza 30) Foreign Application Priority Data tion of a polysaccharide having a rod-like helical struc ture, comprising a step for forcing a solution of the Feb. 16, 1982 JP Japan ................................ 57-23724 polysaccharide in a solvent (solvent A) through a capil lary at a high shear rate, to produce a lower molecular (51) Int. Cl. .............................................. C13K 13/00 weight degraded polysaccharide, which has the same 52 U.S. C. ..................................... 127/36; 127/46.1; repeating unit and the same helical structure, as those of 536/114; 536/124 the original polysaccharide. 58) Field of Search ........................ 127/2, 9, 38, 46.1, 127/55; 536/80, 114, 124; 424/180 9 Claims, 1 Drawing Figure r = shear rate is 7 x lose c 4 OO 3OO 2 OO is 4.5x Iosec OO 4. 8 2 6 Retention time in capillary (XO) sec U.S. Patent Mar. 19, 1985 4,505,757 FIGURE I r = Shedr rate 5ool is 7. x O' sec O 3, 4 OO 3. > 3OO = 2.8 x IO's ec 2 OO = 4.5x Osec OO 4 8 2 6 Retention time in capillary (XO") sec 4,505,757 1. 2 Newtonian fluid, improving the fluidity of a food con METHOD FOR A SPECIFIC taining the polysaccharide. DEPOLYMERIZATION OF A POLYSACCHARDE The depolymerization according to the present in HAVING AROD-LIKE HELICAL vention is performed by forcing a solution of the poly CONFORMATION saccharide to pass through a capillary at a high shear rate, preferably higher than 1x10 sec-1. Examples of BACKGROUND OF THE INVENTION the polysaccharides used in the present method are beta-1,3-D-glucans and xanthan gum. 1. Field of the Invention The depolymerization-efficiency of the present The present invention relates to the specific depolym 10 method was found to become higher, as the concentra erization of a polysaccharide having a rod-like helical tion of the polysaccharide-solution increases, especially conformation. when it is higher than 0.1 wt.%. The addition of a sol 2. Description of the Prior Art vent (solvent B) to the polysaccharide-solution was also Several viscous polysaccharides such as xanthan, found to increase the efficiency of the depolymerization lentinan, schizophyllan, scleroglucan or curdlan, have 15 according to the present method, where solvent B is been found to have two or three stranded helical struc miscible with the solvent (solvent A) of the polysaccha tures. (T. Norisuye, et. al.; J. Polymer Science, Polymer ride-solution and does not dissolve the polysaccharide. Physics Ed. 18, 547-558 (1980): E. D. T. Atkins and K. The present invention was derived from the finding D. Parker; J. Polymer Science Part C. 28, 69-81 (1969); that the treatment of a solution of the polysaccharide T. L. Bluhm and A. Sarko; Can. J. Chem. 55, 293-299 20 under a high shear rate depolymerizes the polysaccha (1977): R. H. Marchessault, et. al; Can. J. Chem. 55, ride in a manner similar to that of the ultrasonic treat 300-303 (1977): E. R. Morris; A.C.S. Symposium Se ment; i.e., only main chain of the polysaccharide but ries, n, 45, 81 (1977): E. R. Morris, et al; J. Mol. Biol. neither other glucosidic linkages nor carbon-carbon 110, 1 (1977)). Exploitation of the potentials of these bonds in the glucose residues are cleaved during the polysaccharides has been investigated and some were 25 present depolymerization treatment. developed as thickening agents for food industry based The helical-structural polysaccharide is known to on their high viscosities, and others were found to have dispersed into single chains in a specific condition, e.g., potent, host-mediated anti-tumor activities. But in some beta-1,3-D-glucan disperses to single chains in dimethyl cases, the extremely high viscosities of their solutions sulfoxide or alkaline solutions. When the dimethyl sulf make their utilizations difficult. 30 oxide solution is diluted with water or the alkaline solu tion is neutralized with acid, the helical structure of the In order to reduce their viscosities properly, we in polysaccharide is not recovered, but, by random associ vented an ultrasonic method for depolymerization of ation, a large aggregate is formed. The present inven the polysaccharides. (Japanese Patent Laid open No. tion is useful only for a solution of the polysaccharide (Kokai) 57335/1977) Our investigations on the mode of 5 having a helical structure, but not for that having a the ultrasonic depolymerization confirmed that it is 3 single chain structure or an aggregated conformation. caused mainly by the cleavages of the main chain of the The present method is capable of overcoming the polysaccharide and that neither side chain nor carbon foregoing disadvantages, such as low efficiency, high carbon bond in glucose residue is cleaved during the noise-level or erosion of the vibrating rod of the ultra sonic depolymerization. Thus, the resulting degraded sonic oscillator, as seen in the ultrasonic depolymeriza polysaccharide consists of the same repeating unit and tion method. also has the same helical conformation, as those of the Acid hydrolysis and enzymic degradation of a poly original polysaccharide. saccharide have been known. Acidihydrolysis cleaves Recently, we found that the ultrasonic depolymeriza equally all glucosidic linkages of the polysaccharide, tion method is not suited for industrial depolymeriza 45 while enzymic degradation causes the hydrolysis of a tion of a large bulk of polysaccharide, because of its low specific glucosidic linkage. But their depolymerization efficiency. The ultrasonic depolymerization method is modes are significantly different from those of ul also involved in high noise-level and erosion of the trasonication and the present method. They liberate vibrating rod of the ultrasonic oscillator. very low molecular weight mono- or oligo-saccharides SUMMARY OF THE INVENTION 50 and cannot afford quantitatively degraded polysaccha ride, which has the same chemical and conformational It is an object of the present invention to depolymer structures as those of the original polysaccharide. ize a polysaccharide having a rod-like helical structure by forcing its solution to flow at a high shear rate. DETAILED DESCRIPTION OF THE Another object of the present invention is to provide 55 PREFERRED EMBODIMENTS a special degraded polysaccharide, which consists of The depolymerization of the polysaccharide is per the same repeating unit and the helical conformation as formed by forcing a solution of the polysaccharide to those of the starting polysaccharide. A solution of the pass through a capillary such as nozzle, slit, or porous degraded polysaccharide exhibits extremely lower vis sintered plate or ceramics, using a high pressure-driving cosity in comparison with that of the starting polysac force. charide, and the polysaccharide still holds the chemical The depolymerization-velocity depends only on the and physical features such as antitumor activity of the value of the shear rate applied, which results from the original polysaccharide except for the molecular weight driving force, pressure, diameter and length of the cap and viscosity. The reduction in the viscosity of the illary used, and the viscosity of the solution. While solution is helpful for its industrial utilization. For exam 65 repetition of the passage of the solution through a capil ple, it makes administration of the polysaccharide easy lary in a certain condition, the molecular weight of the in a case of its clinical uses as an anticancer drug, or a polysaccharide gradually decreases, approaching a min thixotropic solution of the starting polysaccharide turns imum value, from which no further depolymerization 4,505,757 3 4. occurs. The minimum molecular weight also depends rate of the solution was adjusted to each 0.23 cm/sec., on the value of the shear rate applied; higher shear rate 0.90 cm3/sec., 14.5 cm3/sec. and 35.4 cm/sec. by con gives lower minimum molecular weight. trol of the speed of the pump. The shear rate computed Thus, the value of the shear rate applied is a dominant for each flow rate from the following formula was factor for the present method. No substantial depolym 7.1 x 104 sec-1 for 0.23 cm3/sec flow rate, 2.8x10 erization occurs at too low shear rate. Generally, a sec-1 for 0.90 cm3/sec flow rate, 4.5 x 106 sect for shear rate at least higher than 1 x 10'sec is necessary 14.5 cm3/sec flow rate, and 1.1 x 107 sect for 35.4 for the present depolymerization method. cm/sec flow rate, respectively. In order to give such a high shear rate, the pressure 10 applied to the polysaccharide-solution and the cross shear rate = 4 x flow rate sectional area of the capillary are 20-800 kg/cm2 and 1T X (radius of the capillary) 1x10-4-100 mm2, respectively.
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