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(12) Patent Application Publication (10) Pub. No.: US 2005/0112260 A1 Abraham Et Al

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(12) Patent Application Publication (10) Pub. No.: US 2005/0112260 A1 Abraham Et Al US 2005O112260A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2005/0112260 A1 Abraham et al. (43) Pub. Date: May 26, 2005 (54) MONATIN TABLETOPSWEETENER (21) Appl. No.: 10/903,582 COMPOSITIONS AND METHODS OF MAKING SAME (22) Filed: Aug. 2, 2004 (75) Inventors: Timothy W. Abraham, Minnetonka, Related U.S. Application Data MN (US); Douglas C. Cameron, Plymouth, MN (US); Melanie J. (60) Provisional application No. 60/492,014, filed on Aug. Goulson, Dayton, MN (US); Paula M. 1, 2003. Hicks, Eden Prairie, MN (US); Michael O O G. Lindley, Crowthorne (GB); Sara C. Publication Classification McFarlan, St.Paul, MN (US); James 7 R. Millis, Plymouth, MN (US); John s - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - A: Rosazza, Iowa City, IA (US); Lishan ( 2) O O - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - /5 Zhao, Carlsbad, CA (US); David P. Weiner, Del Mar, CA (US) (57) ABSTRACT Correspondence Address: The present invention relates to novel Sweetener composi CARGILL, INCORPORATED tions comprising monatin and methods for making Such LAW/24 compositions. The present invention also relates to Sweet 15407 MCGINTY ROAD WEST ener compositions comprising Specific monatin Stereoiso WAYZATA, MN 55391 (US) mers, Specific blends of monatin Stereoisomers, and/or monatin produced via a biosynthetic pathway in Vivo (e.g., (73) Assignee: Cargill, Inc. inside cells) or in vitro. -- re Tryptophan Indole-3-lactic acid PLP and amino acceptor or NAD(P) or HO and O, and FAD NAD(P) or HO and O, and FMN Indole-3-pyruvate - C3 molecule PLP 2-hydroxy 2-(indol-3-ylmethyl)-4-keto glutaric acid (MP) PLP and amino donor or NAD(P)H +NH3 Patent Application Publication May 26, 2005 Sheet 1 of 14 US 2005/0112260 A1 -- st Tryptophan Indole-3-lactic acid PLP and amino acceptor or NAD(P) or HO and O, and FAD NAD(P) or HO and O, and FMN Indole-3-pyruvate + C3 molecule PLP 2-hydroxy 2-(indol-3-ylmethyl)-4-keto glutaric acid (MP) PLP and amino donor or NAD(P)H +NH3 FIG. 1 Patent Application Publication May 26, 2005 Sheet 2 of 14 US 2005/0112260 A1 U.S. Patent No. 4,371,614 Tryptophan EC 2.6.1.27 tryptophan aminotransferase EC 2.6.1.5 tyrosine (aromatic) aminotransferase EC 1.4.1.19 tryptophan dehydrogenase EC 1.4.1.2-4 glutamate dehydrogenase EC 1.4.1.20 phenylalanine dehydrogenase EC 2.6.1.28 tryptophan-phenylpyruvate transaminase EC 2.6.1.- multiple substrate aminotransferase EC 2.6.1.1 aspartate aminotransferase EC 1.4.3.2 L-amino acid oxidase tryptophan oxidase (no EC number) D-tryptophan aminotransferase (no EC number) EC 1.4.99.1 D-amino acid dehydrogenase EC 1.4.3.3 D-amino acid oxidase 2.6.1.21 D-alanine aminotransferase Indole-3-pyruvate EC 4.1.3.-, 4.1.2.-lyase, synthase EC 4.1.3.16 4-Hydroxy-2-oxoglutarate glyoxylate-lyase EC 4.1.3.17 4-Hydroxy-4-methyl-2-oxoglutarate pyruvate-lyase Chemical aldol condensation 2-hydroxy 2-(indol-3-ylmethyl)-4-ketoglutaric acid EC 2.6.1.27 tryptophan aminotransferase EC 2.6.1.5 tyrosine (aromatic) aminotransferase EC 1.4.1.19 tryptophan dehydrogenase EC 2.6.1.28 tryptophan-phenylpyruvate transaminase EC 2.6.1.- multiple substrate aminotransferase EC 2.6.1.1 aspartate aminotransferase EC 1.4.1.2-4 glutamate dehydrogenase EC 1.4.1.20 phenylalanine dehydrogenase EC 1.4.99.1 D-amino acid dehydrogenase EC 2.6.1.21 D-alanine aminotransferase D-typtophan aminotransferase (no EC number) Monati FIG. 2 Patent Application Publication May 26, 2005 Sheet 3 of 14 US 2005/0112260 A1 FIG 3 Indole-3-lactic acid EC 1.1.1.110 indolelactate dehydrogenase EC 1.1.1.222 R-4-hydroxyphenylactate dehydrogenase EC 1.1.1.2373-(4)-hydroxyphenylpyruvate reductase EC 1.1.1.27, 1.1.1.28, 1.1.2.3 lactate dehydrogenase EC 1.1.1.11 l (3-imidazol-5-yl) lactate dehydrogenase EC 1.1.3.- lactate oxidase Chemical oxidation Indole-3-pyruvate FIG. 4 COOR 2 O COOR2 S COO O -N R3 COOR \ - R - y bh O N N Enolate chemistry R R R =Boc, Cbz, etc. R2 and R Alkyl, Aryl, etc. Patent Application Publication May 26, 2005 Sheet 4 of 14 US 2005/0112260 A1 FIG. 5A Agio? lOO n/z = 293 5O O O 4. 8 2 6 2O 24 Time (min) F.G. 6 OO 293 5 O 50 2OO 250 3OO 350 4OO Patent Application Publication May 26, 2005 Sheet 5 of 14 US 2005/0112260 A1 FIG. 7A O8-Apr-2002 O O A 15:11:01 5O O O 4 8 2 6 2O 24 FG. 7B Time (min)s 92 OO 2 B 168 es O OV) 58 9 50 30 g 174 229 21.212 230 aY4c) O awsw val "Itlar - d. III,na..... all. IV L.-...-L. 275,23.. OO 50 200 250 300 n/z FG. 8 +T OF MS: 124 MCA scans from Sample 7 (293.jd with Tryptophan) of caroto9a.wif... Max 9.3e4 counts. a=3.569708085.37750280e-004, tos-1,246268795.88351580e 4002 r. 293,144 9.0 e4 8-0 ea 7,094 Cargill Sample Sample 293 with Tryptophan as Internal Std 6.0 e4 5.084 4.Oe4 3.0e4 2,084 i 294.1210 1.04 O. -------a------a -------all- ---A------- Patent Application Publication May 26, 2005 Sheet 6 of 14 US 2005/0112260 A1 VB342 10-Jul-2002 13:11:33 O70202a t scans. 1CO FIG. 9A ka 2128 % oria, 1: Scan ES+ 100 FG. 9B 1. % ori E" 1: Scan ES+ 10C o 15 FG.9C % O 2OO ET BOO OOO 12.00 14.00 16.00 t 22.OO 240 Time F.G. 10 O i 14OE--05 O 1.2OE+05 a 1.00E+05 8.00E--04 6.00E+04 5 4.00E+04 w5 2.OOE-04 2 O.OOE+00 -- - - - - S4 4hr 24hr 24hr 48hr 48hr 7Ohr 70hr -2.00E+04 (-) (+) (-) (+) (-) (+) a -4.00E+04 Time Patent Application Publication May 26, 2005 Sheet 7 of 14 US 2005/0112260 A1 FIG. 11 tryptophan tryptophan oxidase O 2 O catalase amino acid oxidase HO 6 2N/2 indole-3-pyruvate pyruvate ProA aldolase monatin precursor (MP) aspartate aspartate aminotransferase Oxaloacetate monatin v Oxaloacetate \, decarboxylase 3. pyruvate + CO Patent Application Publication May 26, 2005 Sheet 8 of 14 US 2005/0112260 A1 F.G. 12 tryptophan tryptophan oxidase or O 5 catalase amino acid Oxidase HO indole-3-pyruvate pyruvate ProA aldolase monatin precursor (MP) lysine lysine &-aminotransferase alysine mOnatin \spontaneous, - H20 1-Piperideine 6-carboxylate Patent Application Publication May 26, 2005 Sheet 9 of 14 US 2005/0112260 A1 FIG. 13 tryptophan O tryptophan oxidase g catalase Or amino acid oxidase HO, indole-3-pyruvate pyruvate ProA aldolase monatin precursor (MP) CO 2 dehydrogenase NADH (reductive amination) . g NH, NAD ) / monatin / Formate dehydrogenase ammonium formate Patent Application Publication May 26, 2005 Sheet 10 of 14 US 2005/0112260 A1 F.G. 14: 14 13 12 11 1O s i? 67 on 5 4. 3 2 1 O O 10 20 30 40 50 60 ppm R,R monatin Patent Application Publication May 26, 2005 Sheet 11 of 14 US 2005/0112260 A1 FIG. 15 12 10 6 Sensory Procedure: Sweetness matching using 20 trained assessors making judgements hin duplicate 2 Test and reference sohutions prepared in citric/citrate buffer at pH32 O 20 40 60 80 100 CONCENTRATION (ppm) Patent Application Publication May 26, 2005 Sheet 12 of 14 US 2005/0112260 A1 F.G. 16 12 O 2B e saccharin / DuBois et a, ACS Sy S Symposium Series 450, > pp. 261-277, 1991 N (stimuli presented in 4 de-lonized water) (stimuli presented in pH 3.2 buffer) 2 O O 250 500 2O 40 60 8O CONCENTRATION (ppm) Patent Application Publication May 26, 2005 Sheet 13 of 14 US 2005/0112260 A1 F.G. 17 WB342 04-Oct 2002 O8:53:24 RM of 1 Cane ES TC 10 S.9ses Standard 1. MRM of ChanneS. 1. TC 2S4S/2R4R 4.36es Standard ne 2. 40 6.0 B.O 10.00 1200 14. 16. BOO 20.OO 22O 24.OO Patent Application Publication May 26, 2005 Sheet 14 of 14 US 2005/0112260 A1 F.G. 18 VB342 O7-Oct-2002 11:37:16 1:MRM of 1 Channel ES+ 100 2R4R 93. % Standard O 1:MRM of Channel ES+ 1G of 2S4S % Standard 2.OO 4. 6.00 B.O 10.00 2.0 14.OO 16.00 18too 20.00 22.0 24.00 e US 2005/0112260 A1 May 26, 2005 MONATIN TABLETOP SWEETENER 0006 Monatin is a naturally-occurring, high intensity COMPOSITIONS AND METHODS OF MAKING Sweetener. Monatin has four stereoisomeric forms: 2R, 4R SAME (the “RR stereoisomer” or “RR monatin”), 2S, 4S (the “S.S stereoisomer” or “S.S monatin”), 2R, 4S (the “R,S stereoi CROSS-REFERENCE TO RELATED Somer” or “R,S monatin”), and 2S, 4R (the “S.R stereoiso APPLICATIONS mer” or “S.R monatin”). As used herein, unless stated 0001) This application claims the benefit of U.S. Provi otherwise, “monatin” refers to all four stereoisomers of sional Patent Application 60/492,014 filed Aug. 1, 2003, the monatin, as well as any blends of any combination of entire disclosure of which is incorporated herein by refer monatin Stereoisomers (e.g., a blend of the R,R and S.S, CCC. Stereoisomers of monatin). 0007 Monatin has an excellent Sweetness quality. Mona FIELD OF INVENTION tin has a flavor profile that is as clean or cleaner that other 0002 The present invention relates to novel Sweetener known high intensity Sweeteners.
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