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Journal of Carbohydrate Chemistry Volume 21, 2002 - Issue 1-2
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Original Articles

SYNTHESIS OF AMINOACYL SUGAR DERIVATIVES AND THEIR TASTE CHARACTERISTICS. I. 2,3-DI- O-AMINOACYL DERIVATIVES OF ALKYL d-GLUCOPYRANOSIDES

Tomoya Machinami Department of Chemistry, College of Science and Engineering, Meisei University, Hino, Tokyo, 191-8506, JapanCorrespondence[email protected]
,
Norihiro Iibuchi Department of Chemistry, College of Science and Engineering, Meisei University, Hino, Tokyo, 191-8506, Japan
,
Takushi Nomura Department of Chemistry, College of Science and Engineering, Meisei University, Hino, Tokyo, 191-8506, Japan
,
Takeshi Mitsumori Department of Chemistry, College of Science and Engineering, Meisei University, Hino, Tokyo, 191-8506, Japan
,
Tetsuo Suami Department of Chemistry, College of Science and Engineering, Meisei University, Hino, Tokyo, 191-8506, Japan
&
Leslie Hough Department of Chemistry, King's College London, University of London, Strand, London, WC2R 2LS, United Kingdom
Pages 131-142 | Received 22 Jan 2001, Accepted 24 Dec 2001, Published online: 28 Oct 2011

REFERENCES

  • Machinami , T. and Suami , T. 1994 . Abstract B1.24, 17th International Carbohydrate Symposium, Ottawa, Canada, July 17–22, 1994 Edited by: Jennings , H. J. Ottawa : National Research Council Canada .
  • a) Shallenberger , R. S. and Acree , T. E. 1967 . Molecular theory of sweet taste . Nature , 216 : 480 – 482 . b) Shallenberger, R.S. Intrinsic chemistry of fructose. Pure Appl. Chem. 1978, 50, 1409–1420. c) Shallenberger, R.S. Taste Chemistry; Blackie Academic and Professional, 1993, pp. 64–73
  • Kier , L. B. 1972 . A molecular theory of sweet taste . J. Pharm. Sci. , 61 ( 9 ) : 1394 – 1397 .
  • Suami , T. and Hough , L. 1991 . Molecular mechanisms of sweet taste 1: sweet and non-sweet tasting amino acids . J. Carbohydr. Chem. , 10 ( 5 ) : 851 – 860 .
  • Suami , T. and Hough , L. 1992 . Molecular mechanisms of sweet taste 2: glucopyranose, fructopyranose and sucrose . J. Carbohydr. Chem. , 11 ( 8 ) : 953 – 967 .
  • Suami , T. and Hough , L. 1993 . Molecular mechanisms of sweet taste 3: aspartame and its non-sweet isomers . Food Chem. , 46 : 235 – 238 .
  • Suami , T. and Hough , L. 1993 . Molecular mechanisms of sweet taste 4: sucrononic acid and a related derivative . Food Chem. , 48 : 267 – 270 .
  • Suami , T. , Hough , L. , Tsuboi , M. , Machinami , T. and Watanabe , N. 1994 . Molecular mechanisms of sweet taste 5: sucralose and its derivatives . J. Carbohydr. Chem. , 13 ( 8 ) : 1079 – 1092 .
  • a) Kinomura , K. , M. Tamura , K. , Oga , T. and Okai , H. 1984 . Synthesis of Methyl 2,3-Di-O-glycyl-α-d-glucopyranoside and 4,6-Di-O-glycyl-2,3-di-O-methyl-α-d-glucopyranoside, and removal of aminoacyl groups from sugar moieties . J. Carbohydr. Chem. , 3 ( 2 ) : 229 – 241 . b) Tamura, M.; Nakatsuka, T.; Kinomura, K.; Okai, H.; Fukui, S. Methyl 2,3-di-O-(l-alanyl)-α-d-glucopyranoside, a new sweet substance. Agric. Biol. Chem., 1985, 49 (3), 891–893. c) Tamura, M.; Shoji, M.; Nakatsuka, T.; Kinomura, K.; Okai, H.; Fukui, S. Methyl 2,3-di-O-(l-α-aminobutyryl)-α-d-glucopyranoside, a new sweet substances and tastes of related compounds of neutral amino acids and d-glucose derivatives. Agric. Biol. Chem. 1985, 49 (9), 2579–2586. d) Tamura, M.; Nakamura, K.; Kinomura, K.; Okai, H. Relationship between taste and structure of O-aminoacyl sugars containing basic amino acids. Biosci. Biotechnol. Biochem. 1993, 57 (1), 20–23.
  • Richtmyer , N. K. 1962 . “ β-d-Altrose ” . In Methods in Carbohydrate Chemistry Edited by: Whistler , R. L. and Wolfrom , M. L. Vol. 1 , 107 – 108 . New York and London : Academic Press .
  • Pelyvas , I. F. , Lindhorst , T. K. , Streicher , H. and Thiem , J. 1991 . Regioselective acylation of carbohydrates with 1-acyloxy-1H-benzotriazoles . Synthesis , : 1015 – 1018 .
  • Lindberg , B. 1948 . Acta Chim. Scand. , 2 : 426 – 429 .
  • As a preliminary result, methyl 3,4-di-O-(l-alanyl)-α-d-glucopyranoside, mp 170°C (dec.); [α]D25+121° (c 1.0, water), derived from methyl 2-O-benzoyl-4,6-di-O-benzylidene-α-d-glucopyranoside11 (8.5%, in 7 steps reactions), was not sweet.

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