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2008 | OriginalPaper | Buchkapitel

Degradations and Rearrangement Reactions

verfasst von : Jianbo Zhang

Erschienen in: Glycoscience

Verlag: Springer Berlin Heidelberg

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Abstract

This section deals with recent reports concerning degradation and rearrangement reactions of free sugars as well as some glycosides. The transformations are classified in chemical and enzymatic ways. In addition, the Maillard reaction will be discussed as an example of degradation and rearrangement transformation and its application in current research in the fields of chemistry and biology.

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Vorheriges Kapitel C=C Bond Formation

Nächstes Kapitel Glycosyl Halides

Solomons TWG, Fryhle CB (2002) Organic chemistry. Wiley, New York

Bruice PY (2004) Organic chemistry. Pearson/Prentice Hall, Upper Saddle River, NJ

Stütz AE (2001) Glycoscience: epimerisation, isomerisation and rearrangement reactions of carbohydrates. Springer, Berlin, Heidelberg, New York

Lindhorst TK (2003) Essentials of carbohydrate chemistry and biochemistry. Wiley-VCH, Weinheim

Levy DE, Fügedi P (2006) The organic chemistry of sugars. Taylor & Francis, Boca Raton, FL

Sun Y, Cheng J (2002) Biores Technol 83:1

Wolfenden R, Lu X, Young G (1998) J Am Chem Soc 120:6814

Chenault HK, Chafin LF (1998) J Org Chem 63:833

Kirby AJ, Stromberg R (1994) J Chem Soc-Chem Comm: 709

10.

Camilleri P, Jones RFD, Kirby AJ, Stromberg R (1994) J Chem Soc-Perkin Trans 2:2085

11.

Sidelmann UG, Hansen SH, Gavaghan C, Carless HAJ, Lindon J, Farrant R, Wilson ID, Nicholson JK (1996) Anal Chem 68:2564

12.

ManleyHarris M, Richards GN (1996) Carbohydr Res 287:183

13.

Sinnott ML (1990) Chem Rev 90:1171

14.

Kaczmarek J, Kaczynski Z, Trumpakaj Z, Szafranek J, Bogalecka M, Lonnberg H (2000) Carbohydr Res 325:16

15.

Horenstein BA, Bruner M (1996) J Am Chem Soc 118:10371

16.

Chong AK, Pegg MS, Taylor NR, von Itzstein M (1992) Eur J Biochem 207:335

17.

Davies GJ, Mackenzie L, Varrot A, Dauter M, Brzozowski AM, Schulein M, Withers SG (1998) Biochemistry 37:11707

18.

Nagano N, Noguchi T, Akiyama Y (2007) Proteins Struct Funct Bioinform 66:147

19.

Crennell SJ, Garman EF, Laver WG, Vimr ER, Taylor GL (1993) Proc Natl Acad Sci USA 90:9852

20.

Guo X, Sinnott ML (1993) Biochem J 296(Pt2):291

21.

Ashwell M, Sinnott ML, Zhang Y (1994) J Org Chem 59:7539

22.

Ashwell M, Guo X, Sinnott ML (1992) J Am Chem Soc 114:10158

23.

Pitson SM, Mutter M, van den Broek LA, Voragen AG, Beldman G (1998) Biochem Biophys Res Commun 242:552

24.

Biely P, Benen J, Heinrichova K, Kester HC, Visser J (1996) FEBS Lett 382:249

25.

Schultz PG, Lerner RA (1995) Science 269:1835

26.

Yu J, Choi SY, Moon KD, Chung HH, Youn HJ, Jeong S, Park H, Schultz PG (1998) Proc Natl Acad Sci USA 95:2880

27.

Yu S, Ahmad T, Kenne L, Pedersen M (1995) Biochim Biophys Acta 1244:1

28.

Richard GT, Yu S, Monsan P, Remaud‐Simeon M, Morel S (2005) Carbohydr Res 340:395

29.

Yu S, Kenne L, Pedersen M (1993) Biochim Biophys Acta 1156:313

30.

Saddler JN, Penner MH (1995) Am Chem Soc Meeting. Enzymatic degradation of insoluble carbohydrates. American Chemical Society, Washington, DC

31.

Horn SJ, Sikorski P, Cederkvist JB, Vaaje-Kolstad G, Sorlie M, Synstad B, Vriend G, Varum KM, Eijsink VG (2006) Proc Natl Acad Sci USA 103:18089

32.

National Research Council (US) Committee on Bioprocess Engineering (1992) Putting biotechnology to work: bioprocess engineering. National Academy of Sciences, Washington, DC

33.

Mulimani VH, Ramalingam R (1995) Biochem Mol Biol Int 36:897

34.

Kulkarni DS, Kapanoor SS, Girigouda K, Kote NV, Mulimani VH (2006) Biotechnol Appl Biochem 45:51

35.

Hollingsworth RI, Wang G (2000) Chem Rev 100:4267

36.

Nolasco J, De Massaguer PR (2006) J Food Proc Eng 29:462

37.

Hollnagel A, Kroh LW (2000) J Agricult Food Chem 48:6219

38.

Miyazawa T, Ohtsu S, Nakagawa Y, Funazukuri T (2006) J Mat Sci 41:1489

39.

Srokol Z, Bouche AG, van Estrik A, Strik RCJ, Maschmeyer T, Peters JA (2004) Carbohydr Res 339:1717

40.

Griebl A, Lange T, Weber H, Milacher W, Sixta H (2006) Macromol Symp 232:107

41.

Kruse A, Gawlik A (2003) Ind Eng Chem Res 42:267

42.

Hashaikeh R, Fang Z, Butler IS, Kozinski JA (2005) Proc Combustion Institute 30:2231

43.

Chheda JN, Roman-Leshkov Y, Dumesic JA (2007) Green Chem 9:342

44.

Sanderson K (2006) Nature 444:673

45.

Hayes MH (2006) Nature 443:144

46.

Kruse A, Maniam P, Spieler F (2007) Ind Eng Chem Res 46:87

47.

Mark J, Pollien P, Lindinger C, Blank I, Mark T (2006) J Agricult Food Chem 54:2786

48.

Fan XT (2005) J Agricult Food Chem 53:7826

49.

Ginz M, Balzer HH, Bradbury AGW, Maier HG (2000) Eur Food Res Technol 211:404

50.

Arya M, Rao LJM (2007) Crit Rev Food Sci Nutrit 47:51

51.

Burde RDL, Crayton F, Bavley A (1962) Nature 196:166

52.

Qian X, Nimlos MR, Johnson DK, Himmel ME (2005) Appl Biochem Biotechnol 121–124:989

53.

Buskas T, Konradsson P (2000) J Carbohydr Chem 19:25

54.

Antal MJ Jr, Mok WS, Richards GN (1990) Carbohydr Res 199:91

55.

Halliday GA, Young RJ Jr, Grushin VV (2003) Org Lett 5:2003

56.

Hauck T, Landmann C, Bruhlmann F, Schwab W (2003) J Agric Food Chem 51:1410

57.

deGoede ATJW, vanDeurzen MPJ, vanderLeij IG, vanderHeijden AM, Baas JMA, vanRantwijk F, vanBekkum H (1996) J Carbohydr Chem 15:331

58.

Cancilla MT, Penn SG, Lebrilla CB (1998) Anal Chem 70:663

59.

Yang BY, Montgomery R (2007) Bioresour Technol 98:3084

60.

T'i VTU, Pisarnitskii AF (1998) Appl Biochem Microbiol 34:106

61.

Manini P, La Pietra P, Panzella L, Napolitano A, d'Ischia M (2006) Carbohydr Res 341:1828

62.

Hourdin GL, Germain A, Moreau C, Fajula F (2002) J Catal 209:217

63.

van den Berg R, Peters JA, van Bekkum H (1995) Carbohydr Res 267:65

64.

Rangappa KS, Raghavendra MP, Mahadevappa DS, Gowda DC (1998) Carbohydr Res 306:57

65.

Hollingsworth RI (1996) Biotechnol Annu Rev 2:281

66.

Hollingsworth RI (1999) J Org Chem 64:7633

67.

Stapley JA, BeMiller JN (2007) Carbohydr Res 342:407

68.

Hourdin G, Germain A, Moreau C, Fajula F (2000) Catal Lett 69:241

69.

Fischer K, Bipp HP (2005) Biores Technol 96:831

70.

Niu W, Molefe MN, Frost JW (2003) J Am Chem Soc 125:12998

71.

Service RF (2007) Science 315:1488

72.

Champagne P (2007) Resour Conserv Recy 50:211

73.

Kakinuma K, Li HY (1989) Tetrahedron Lett 30:4157

74.

Taillefumier C, Chapleur Y (2004) Chem Rev 104:263

75.

Sasaki M, Higashi M, Masu H, Yamaguchi K, Takeda K (2005) Org Lett 7:5913

76.

Bertrand P, Gesson JP, Renoux B, Tranoy I (1995) Tetrahedron Lett 36:4073

77.

Halcomb RL, Boyer SH, Wittman MD, Olson SH, Denhart DJ, Liu KKC, Danishefsky SJ (1995) J Am Chem Soc 117:5720

78.

Modica E, Compostella F, Colombo D, Franchini L, Cavallari M, Mori L, De Libero G, Panza L, Ronchetti F (2006) Org Lett 8:3255

79.

Jaunzeme I, Jirgensons A (2005) Synlett: 2984

80.

Montero A, Mann E, Herradon B (2005) Tetrahedron Lett 46:401

81.

Banaszek A, Pakulski Z, Zamojski A (1995) Carbohydr Res 279:173

82.

Ichikawa Y, Kobayashi C, Isobe M (1996) J Chem Soc-Perkin Trans 1:377

83.

Ichikawa Y, Kobayashi C, Isobe M (1994) Synlett: 919

84.

Oishi T, Ando K, Inomiya K, Sato H, Iida M, Chida N (2002) Org Lett 4:151

85.

Werschkun B, Thiem J (2001) Glycoscience: Epimerisation, Isomerisation and Rearrangement Reactions of Carbohydrates. Topics in Current Chemistry Vol 215. Springer-Verlag, Berlin, Heidelberg, p 293

86.

Sudha AVRL, Nagarajan M (1998) Chem Comm 925

87.

Balasubramanian KK, Ramesh NG, Pramanik A, Chandrasekhar J (1994) J Chem Soc-Perkin Trans 2:1399

88.

Kuhn C, Legouadec G, Skaltsounis AL, Florent JC (1995) Tetrahedron Lett 36:3137

89.

Overman LE, Shim J (1993) J Org Chem 58:4662

90.

Deng W, Overman LE (1994) J Am Chem Soc 116:11241

91.

Knight SD, Overman LE, Pairaudeau G (1995) J Am Chem Soc 117:5776

92.

Agami C, Couty F, Lin J, Mikaeloff A (1993) Synlett: 349

93.

Agami C, Couty F, Puchot‐Kadouri C (1998) Synlett: 449

94.

Oberdorfer F, Haeckel R, Lauer G (1998) Synthesis‐Stuttgart: 201

95.

Mundorff EC, Hanson MA, Varvak A, Ulrich H, Schultz PG, Stevens RC (2000) Biochemistry 39:627

96.

Black KA, Leach AG, Kalani MY, Houk KN (2004) J Am Chem Soc 126:9695

97.

Yokoyama H, Otaya K, Yamaguchi S, Hirai Y (1998) Tetrahedron Lett 39:5971

98.

Zamojski A (2002) Polish J Chem 76:1053

99.

Yokoyama H, Ejiri H, Miyazawa M, Yamaguchi S, Hirai Y (2007) Tetrahedron: Asymmetry 18:852

100.

Muzart J (2005) Tetrahedron 61:4179

101.

Mcdonald FE, Gleason MM (1995) Angew Chem Int Ed Engl 34:350

102.

Castro S, Peczuh MW (2005) J Org Chem 70:3312

103.

Redlich H (1994) Angew Chem 106:1407

104.

Collins P, Ferrier RJ (1995) Monosaccharides: their chemistry and their roles in natural products. Wiley, New York

105.

Tatsuta K, Hosokawa S (2006) Sci Technol Adv Mater 7:397

106.

Ponten F, Magnusson G (1994) Acta Chemica Scand 48:566

107.

Ito H (2003) Yakugaku Zasshi-J Pharmaceut Soc Japan 123:933

108.

Ito H, Motoki Y, Taguchi T, Hanzawa Y (1993) J Am Chem Soc 115:8835

109.

Jenkins DJ, Riley AM, Potter BVL (1996) J Org Chem 61:7719

110.

Bettelli E, D'Andrea P, Mascanzoni S, Passacantilli P, Piancatelli G (1998) Carbohydr Res 306:221

111.

Estevez JC, Saunders J, Besra GS, Brennan PJ, Bash RJ, Fleet GWJ (1996) Tetrahedron: Asymmetry 7:383

112.

Bichard CJF, Brandstetter TW, Estevez JC, Fleet GWJ, Hughes DJ, Wheatley JR (1996) J Chem Soc, Perkin Trans 1: Organic and Bio-Organic Chemistry: 2151

113.

Binkley RW, Ambrose MG (1984) J Carbohydr Chem 3:1

114.

Binkley RW (1992) J Org Chem 57:2353

115.

Wang YF, Fleet GWJ, Zhao LX (1998) Carbohydr Res 307:159

116.

Fuzier M, Le Merrer Y, Depezay J‑C (1995) Tetrahedron Lett 36:6443

117.

Poitout L, LeMerrer Y, Depezay JC (1996) Tetrahedron Lett 37:1613

118.

Charette AB, Cote B (1993) J Org Chem 58:933

119.

Jeong LS, Moon HR, Yoo SJ, Lee SN, Chun MW, Lim YH (1998) Tetrahedron Lett 39:5201

120.

Welch JT, Svahn B‑M, Eswarakrishnan S, Hutchinson JP, Zubieta J (1984) Carbohydrate Research 132:221

121.

Baudry M, Barberousse V, Descotes G, Faure R, Pires J, Praly JP (1998) Tetrahedron 54:7431

122.

Goebel M, Nothofer HG, Ross G, Ugi I (1997) Tetrahedron 53:3123

123.

Holton RA, Somoza C, Kim HB, Liang F, Biediger RJ, Boatman PD, Shindo M, Smith CC, Kim SC, Nadizadeh H, Suzuki Y, Tao CL, Vu P, Tang SH, Zhang PS, Murthi KK, Gentile LN, Liu JH (1994) J Am Chem Soc 116:1597

124.

Lee SD, Chan TH, Kwon KS (1984) Tetrahedron Lett 25:3399

125.

Csuk R, Fuerstner A, Weidmann H (1986) J Carbohydr Chem 5:271

126.

Curran DP, Suh Y‑G (1987) Carbohydr Res 171:161

127.

Fredenhagen A, Peter HH (1996) Tetrahedron 52:1235

128.

Stoltz BM, Wood JL (1996) Tetrahedron Lett 37:3929

129.

Avalos M, Babiano R, Cabanillas A, Cintas P, Higes FJ, Jimenez JL, Palacios JC (1996) J Org Chem 61:3738

130.

Hoberg JO, Bozell JJ (1995) Tetrahedron Lett 36:6831

131.

Hoberg JO (1997) J Org Chem 62:6615

132.

Boyer FD, Lallemand JY (1994) Tetrahedron 50:10443

133.

Ramana CV, Murali R, Nagarajan M (1997) J Org Chem 62:7694

134.

Wender PA, Jesudason CD, Nakahira H, Tamura N, Tebbe AL, Ueno Y (1997) J Am Chem Soc 119:12976

135.

Chen XT, Gutteridge CE, Bhattacharya SK, Zhou BS, Pettus TRR, Hascall T, Danishefsky SJ (1998) Angew Chem Int Ed 37:185

136.

Xu YM, Zhou WS (1997) J Chem Soc-Perkin Trans 1:741

137.

Marshall JA, Tang Y (1994) J Org Chem 59:1457

138.

Kim DK, Kim GH, Kim YW (1996) J Chem Soc-Perkin Trans 1:803

139.

Tatsuta K (1998) J Synth Org Chem Japan 56:714

140.

Boyer FD, Pancrazi A, Lallemand JY (1995) Synth Commun 25:1099

141.

Chen YW, Vogel P (1994) J Org Chem 59:2487

142.

Shilvock JP, Fleet GWJ (1998) Synlett: 554

143.

Beacham AR, Smelt KH, Biggadike K, Britten CJ, Hackett L, Winchester BG, Nash RJ, Griffiths RC, Fleet GWJ (1998) Tetrahedron Lett 39:151

144.

Poitout L, LeMerrer Y, Depezay JC (1996) Tetrahedron Lett 37:1609

145.

Ernholt BV, Thomsen IB, Jensen KB, Bols M (1999) Synlett: 701

146.

Lohse A, Jensen KB, Bols M (1999) Tetrahedron Lett 40:3033

147.

Andreassen V, Svensson B, Bols M (2001) Synthesis‐Stuttgart: 339

148.

Moriyama H, Tsukida T, Inoue Y, Kondo H, Yoshino K, Nishimura SI (2003) Bioorg Med Chem Lett 13:2737

149.

Tschamber T, Gessier F, Neuburger M, Gurcha SS, Besra GS, Streith J (2003) Eur J Org Chem: 2792

150.

Fuentes J, Sayago FJ, Illangua JM, Gasch C, Angulo M, Pradera MA (2004) Tetrahedron‐Asymmetry 15:603

151.

Tsukida T, Moriyama H, Inoue Y, Kondo H, Yoshino K, Nishimura SI (2004) Bioorg Med Chem Lett 14:1569

152.

Ichikawa Y, Osada M, Ohtani II, Isobe M (1997) J Chem Soc-Perkin Trans 1:1449

153.

Blanco JLJ, Diaz Prez VM, Mellet CO, Fuentes J, Garcia Fernandez JM, Diaz Arribas JC, Canada FJ (1997) Chem Comm (Cambridge): 1969

154.

Goti A, Cacciarini M, Cardona F, Cordero FM, Brandi A (2001) Org Lett 3:1367

155.

Overkleeft HS, Bruggeman P, Pandit UK (1998) Tetrahedron Lett 39:3869

156.

Haakansson AE, Palmelund A, Holm H, Madsen R (2006) Chemistry-A Eur J 12:3243

157.

Kotha S, Mandal K, Tiwari A, Mobin SM (2006) Chemistry 12:8024

158.

Andresen TL, Skytte DM, Madsen R (2004) Org Biomol Chem 2:2951

159.

Ovaa H, Lastdrager B, Codee JDC, van der Marel GA, Overkleeft HS, van Boom JH (2002) J Chem Soc-Perkin Trans 1:2370

160.

Yamazaki T, Mizutani K, Kitazume T (1996) ACS Symp Series 639:105

161.

Dondoni A, Catozzi N, Marra A (2004) J Org Chem 69:5023

162.

Pradera MA, Sayago FJ, Illangua JM, Gasch C, Fuentes J (2003) Tetrahedron Lett 44:6605

163.

Fuentes J, Illangua JM, Sayago FJ, Angulo M, Gasch C, Pradera MA (2004) Tetrahedron‐Asymmetry 15:3783

164.

Dhavale DD, Jachak SM, Karche NP, Trombini C (2004) Tetrahedron 60:3009

165.

Sun H, Abboud KA, Horenstein NA (2005) Tetrahedron 61:10462

166.

Parr IB, Horenstein BA (1997) J Org Chem 62:7489

167.

Castro S, Peczuh Mark W (2005) J Org Chem 70:3312

168.

Foulard G, Brigaud T, Portella C (1997) J Org Chem 62:9107

169.

Momotake A, Mito J, Yamaguchi K, Togo H, Yokoyama M (1998) J Org Chem 63:7207

170.

Zou W (2005) Curr Topic Med Chem 5:1363

171.

Lin C‑H, Lin H‑C, Yang W‑B (2005) Curr Topic Med Chem (Sharjah, United Arab Emirates) 5:1431

172.

Lee DYW, He MS (2005) Curr Topic Med Chem 5:1333

173.

Bililign T, Griffith BR, Thorson JS (2005) Nat Prod Report 22:742

174.

Sharma GVM, Krishna PR (2004) Curr Org Chem 8:1187

175.

Gascon-Lopez M, Motevalli M, Paloumbis G, Bladon P, Wyatt PB (2003) Tetrahedron 59:9349

176.

Cipolla L, La Ferla B, Nicotra F (1998) Carbohydr Polym 37:291

177.

Cipolla L, Peri F, La Ferla B, Redaelli C, Nicotra F (2005) Curr Org Synth 2:153

178.

Johnson CR, Johns BA (1997) J Org Chem 62:6046

179.

Hashimoto M, Terashima S (1994) Chem Lett: 1001

180.

Brochard L, Lorin C, Spiess N, Rollin P (1998) Tetrahedron Lett 39:4267

181.

Jun JG, Lee DW, Mundy BP (1998) Synth Comm 28:2499

182.

Wei BG, Chen J, Huang PQ (2006) Tetrahedron 62:190

183.

Pelyvas IF, Madi-Puskas M, Toth ZG, Varga Z, Hornyak M, Batta G, Sztaricskai F (1995) J Antibiotics 48:683

184.

Zhou J, Wang G, Zhang L‑H, Ye X‑S (2006) Curr Org Chem 10:625

185.

Ferrier RJ, Hoberg JO (2003) Advances in Carbohydrate Chemistry and Biochemistry, Vol 58, Academic Press, San Diego, London, 58:55

186.

Chida N, Ohtsuka M, Ogura K, Ogawa S (1991) Bull Chem Soc Japan 64:2118

187.

Wang A, Auzanneau FI (2007) J Org Chem 72:3585

188.

Chida N, Takeoka J, Ando K, Tsutsumi N, Ogawa S (1996) Tennen Yuki Kagobutsu Toronkai Koen Yoshishu 38:259

189.

Letellier P, Ralainirina R, Beaupere D, Uzan R (1994) Tetrahedron Lett 35:4555

190.

Letellier P, Ralainairina R, Beaupere D, Uzan R (1997) Synthesis‐Stuttgart: 925

191.

Letellier P, ElMeslouti A, Beaupere D, Uzan R (1996) Synthesis‐Stuttgart: 1435

192.

Iimori T, Takahashi H, Ikegami S (1996) Tetrahedron Lett 37:649

193.

Takahashi H (2001) Yuki Gosei Kagaku Kyokaishi 59:484

194.

Takahashi H (2002) Yakugaku Zasshi-J Pharmaceut Soc Japan 122:755

195.

Miyazaki H, Kobayashi Y, Shiozaki M, Ando O, Nakajima M, Hanzawa H, Haruyama H (1995) J Org Chem 60:6103

196.

Friestad GK, Branchaud BP (1997) Tetrahedron Lett 38:5933

197.

Das SK, Mallet JM, Sinay P (1997) Angew Chem Int Ed Engl 36:493

198.

Sollogoub M, Mallet JM, Sinay P (2000) Angew Chem Int Ed Engl 39:362

199.

Sollogoub M, Sinay P (2006) Organic Chemistry of Sugars: 349

200.

Petasis NA, Yao X (2001) Abstr Pap Am Chem Soc 222:U99

201.

Chung S‑K, Yu S‑H (1996) Bioorg Med Chem Lett 6:1461

202.

Jia C, Pearce AJ, Bleriot Y, Zhang Y, Zhang L‑H, Sollogoub M, Sinay P (2004) Tetrahedron: Asymmetry 15:699

203.

Strukul G (1998) Angew Chem Int Ed 37:1199

204.

Mereyala HB, Guntha S (1995) Tetrahedron 51:1741

205.

Zhou H, Wang GN, Zhang LH, Ye XS (2006) Curr Org Chem 10:625

206.

Bennett SM, Biboutou RK, Zhou ZH, Pion R (1998) Tetrahedron 54:4761

207.

Grove JJC, Holzapfel CW (1997) Tetrahedron Lett 38:7429

208.

CronjeGrove JJ, Holzapfel CW, Williams DBG (1996) Tetrahedron Lett 37:1305

209.

Chiara JL, Martinez S, Bernabe M (1996) J Org Chem 61:6488

210.

Sano H, Sugai S (1995) Tetrahedron‐Asymmetry 6:1143

211.

deArmas P, GarciaTellado F, MarreroTellado JJ, Robles J (1997) Tetrahedron Lett 38:8081

212.

Lewis BE, Choytun N, Schramm VL, Bennet AJ (2006) J Am Chem Soc 128:5049

213.

Liu FW, Zhang YB, Liu HM, Song XP (2005) Carbohydr Res 340:489

214.

Pacsu E (1930) J Am Chem Soc 52:2563

215.

Pacsu J (1928) Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen 61B:1508

216.

Capozzi G, Mannocci F, Menichetti S, Nativi C, Paoletti S (1997) Chem Comm: 2291

217.

Ellervik U, Jansson K, Magnusson G (1998) J Carbohydr Chem 17:777

218.

Csuk R, Schaade M (1994) Tetrahedron 50:3333

219.

Boons GJ, Stauch T (1996) Synlett: 906

220.

Kim JM, Roy R (1997) J Carbohydr Chem 16:1281

221.

Maunier V, Boullanger P, Lafont D (1997) J Carbohydr Chem 16:231

222.

Gervay J, Nguyen TN, Hadd MJ (1997) Carbohydr Res 300:119

223.

Fabian MA, Perrin CL, Sinnott ML (1994) J Am Chem Soc 116:8398

224.

Vaino AR, Szarek WA (2001) J Org Chem 66:1097

225.

Grundberg H, Eriksson‐Bajtner J, Bergquist KE, Sundin A, Ellervik U (2006) J Org Chem 71:5892

226.

Vaino AR, Chan SSC, Szarek WA, Thatcher GRJ (1996) J Org Chem 61:4514

227.

Skorupowa E, Dmochowska B, Madaj J, Kasprzykowski F, Sokolowski J, Wisniewski A (1998) J Carbohydr Chem 17:49

228.

Ren RXF, Chaudhuri NC, Paris PL, Rumney S, Kool ET (1996) J Am Chem Soc 118:7671

229.

Yokoyama M, Nomura M, Togo H, Seki H (1996) J Chem Soc-Perkin Trans 1:2145

230.

Di Florio R, Rizzacasa MA (1998) J Org Chem 63:8595

231.

Brandstetter TW, Kim YH, Son JC, Taylor HM, Lilley PMD, Watkin DJ, Johnson LN, Oikonomakos NG, Fleet GWJ (1995) Tetrahedron Lett 36:2149

232.

Leeuwenburgh MA, Timmers CM, vanderMarel GA, vanBoom JH, Mallet JM, Sinay PG (1997) Tetrahedron Lett 38:6251

233.

Gervay J, Hadd MJ (1997) J Org Chem 62:6961

234.

Vedso P, Chauvin R, Li Z, Bernet B, Vasella A (1994) Helv Chim Acta 77:1631

235.

Barker JL, Frost JW (2001) Biotechnol Bioeng 76:376

236.

Zhu LZ, Talukdar A, Zhang GS, Kedenburg JP, Wang PG (2005) Synlett: 1547

237.

Rowe D (2004) Chem Biodiversity 1:2034

238.

vanDeurzen MPJ, vanRantwijk F, Sheldon RA (1997) J Carbohydr Chem 16:299

239.

Mathews WB, Zajac WW (1995) J Carbohydr Chem 14:287

240.

Devianne G, Escudier JM, Baltas M, Gorrichon L (1995) J Org Chem 60:7343

241.

Lee CK, Kim EJ, Lee ISH (1998) Carbohydr Res 309:243

242.

Diehl V, Cuny E, Lichtenthaler FW (1998) Heterocycles 48:1193

243.

Oikawa N, Muller C, Kunz M, Lichtenthaler FW (1998) Carbohydr Res 309:269

244.

Sun XL, Kai T, Takayanagi H, Furuhata K (1997) J Carbohydr Chem 16:541

245.

Sano H, Mio S, Kitagawa J, Sugai S (1994) Tetrahedron‐Asymmetry 5:2233

246.

Chaudhari VD, Kumar KSA, Dhavale DD (2006) Tetrahedron 62:4349

247.

Kozlowski JS, Marzabadi CH, Rath NP, Spilling CD (1997) Carbohydr Res 300:301

248.

Mauron J (1981) Prog Food Nutr Sci 5:5

249.

Ledl F, Beck J, Sengl M, Osiander H, Estendorfer S, Severin T, Huber B (1989) Prog Clin Biol Res 304:23

250.

John WG, Lamb EJ (1993) Eye 7(Pt2):230

251.

Gerrard J (2005) The Maillard reaction: chemistry, biochemistry and implications by Harry Nursten. Royal Society of Chemistry

252.

Erbersdobler HF, Somoza V (2007) Mol Nutr Food Res 51:423

253.

Charissou A, Ait-Ameur L, Birlouez‐Aragon I (2007) J Agric Food Chem 55:4532

254.

van Boekel MA (2006) Biotechnol Adv 24:230

255.

Kato A (2002) Food Sci Technol Res 8:193

256.

Chen CQ, Robbins E (2000) ACS Symp Series 754:286

257.

Gerrard JA (2006) Trends Food Sci Technol 17:324

258.

Tuohy KM, Hinton DJ, Davies SJ, Crabbe MJ, Gibson GR, Ames JM (2006) Mol Nutr Food Res 50:847

259.

Sun Y, Hayakawa S, Chuamanochan M, Fujimoto M, Innun A, Izumori K (2006) Biosci Biotechnol Biochem 70:598

260.

Saraiva MA, Borges CM, Florencio MH (2006) J Mass Spectrom 41:755

261.

Robert L, Labat-Robert J (2006) Pathol Biol 54:371

262.

Reddy VP, Beyaz A (2006) Drug Discov Today 11:646

263.

Peyroux J, Sternberg M (2006) Pathol Biol (Paris) 54:405

264.

Somoza V (2005) Mol Nutrit Food Res 49:663

265.

Baynes JW (2000) Biogerontology 1:235

266.

Colaco CA (1993) J R Soc Med 86:243

267.

Wirth DD, Baertschi SW, Johnson RA, Maple SR, Miller MS, Hallenbeck DK, Gregg SM (1998) J Pharm Sci 87:31

268.

Howard MJ, Smales CM (2005) J Biol Chem 280:22582

269.

Rahbar S (2005) Ann NY Acad Sci 1043:9

270.

Monnier VM, Stevens VJ, Cerami A (1981) Prog Food Nutr Sci 5:315

271.

Gottlieb Sheldon H (2002) Diabetes Forecast 55:34

272.

Stitt Alan W (2005) Ann NY Acad Sci 1043:582

273.

Mossine VV, Glinsky GV, Barnes CL, Feather MS (1995) Carbohydr Res 266:5

274.

Mossine VV, Barnes CL, Mawhinney TP (2007) Carbohydr Res 342:131

275.

Yaylayan VA, Huyghues‐Despointes A (1996) Carbohydr Res 286:179

276.

Ge SJ, Lee TC (1996) J Agric Food Chem 44:1053

277.

Yaylayan VA, Huyghues‐Despointes A (1994) Crit Rev Food Sci Nutrit 34:321

278.

Niwa T, Takeda N, Miyazaki T, Yoshizumi H, Tatematsu A, Maeda K, Ohara M, Tomiyama S, Niimura K (1995) Nephron 69:438

279.

Yamada H, Miyata S, Igaki N, Yatabe H, Miyauchi Y, Ohara T, Sakai M, Shoda H, Oimomi M, Kasuga M (1994) J Biol Chem 269:20275

280.

Hirsch J, Petrakova E, Feather MS (1992) Carbohydr Res 232:125

281.

Hirsch J, Petrakova E, Feather MS, Barnes CL (1995) Carbohydr Res 267:17

282.

Zyzak DV, Richardson JM, Thorpe SR, Baynes JW (1995) Arch Biochem Biophys 316:547

283.

Hayase F, Shibuya T, Sato J, Yamamoto M (1996) Biosci Biotechnol Biochem 60:1820

284.

Hayase F, Nagaraj RH, Miyata S, Njoroge FG, Monnier VM (1989) J Biol Chem 264:3758

285.

Yaylayan VA, Keyhani A (1999) J Agric Food Chem 47:3280

286.

Kim SW, Rogers QR, Morris JG (1996) J Nutr 126:195

287.

Hiramoto K, Aso-o R, Ni-iyama H, Hikage S, Kato T, Kikugawa K (1996) Mutat Res 359:17

288.

Hiramoto K, Ishihara A, Sakui N, Daishima S, Kikugawa K (1998) Biol Pharm Bull 21:102

289.

Hiramoto K, Kato T, Kikugawa K (1993) Mutat Res 285:191

290.

Hiramoto K, Nasuhara A, Michikoshi K, Kato T, Kikugawa K (1997) Mutat Res 395:47

291.

Hiramoto K, Sekiguchi K, Aso OR, Ayuha K, Ni-Iyama H, Kato T, Kikugawa K (1995) Food Chem Toxicol 33:803

292.

Hiramoto S, Itoh K, Shizuuchi S, Kawachi Y, Morishita Y, Nagase M, Suzuki Y, Nobuta Y, Sudou Y, Nakamura O, Kagaya I, Goshima H, Kodama Y, Icatro Faustino C, Koizumi W, Saigenji K, Miura S, Sugiyama T, Kimura N (2004) Helicobacter 9:429

293.

Lertsiri S, Fujimoto K, Miyazawa T (1995) Biochim Biophys Acta 1245:278

294.

Lertsiri S, Maungma R, Assavanig A, Bhumiratana A (2001) J Food Process Preserv 25:149

295.

Lertsiri S, Oak JH, Nakagawa K, Miyazawa T (2002) Biochim Biophys Acta 1573:48

296.

Lertsiri S, Oak J‑H, Nakagawa K, Miyazawa T (2002) Biochimica et Biophysica Acta, General Subjects 1573:48

297.

Lertsiri S, Shiraishi M, Miyazawa T (1998) Biosci Biotechnol Biochem 62:893

298.

Surh YJ, Liem A, Miller JA, Tannenbaum SR (1994) Carcinogenesis 15:2375

299.

Tressi R, Piechotta CT, Rewicki D, Krause E (2002) Int Congr Series 1245:203

300.

Jenq SN, Tsai SJ, Lee H (1994) Mutagenesis 9:483

301.

Friedman M (1996) J Agric Food Chem 44:631

302.

Vertesy L, Fehlhaber HW, Kogler H, Schindler PW (1996) Liebigs Annalen: 121

303.

Ukeda H, Hasegawa Y, Ishi T, Sawamura M (1997) Biosci Biotechnol Biochem 61:2039

304.

Ukeda H, Shimamura T, Tsubouchi M, Harada Y, Nakai Y, Sawamura M (2002) Anal Sci 18:1151

305.

Buttner U, Gerum F, Severin T (1997) Carbohydr Res 300:265

306.

Buttner U, Ochs S, Severin T (1996) Carbohydr Res 291:175

307.

Ahmed MU, Dunn JA, Walla MD, Thorpe SR, Baynes JW (1988) J Biol Chem 263:8816

308.

Ahmed MU, Thorpe SR, Baynes JW (1986) J Biol Chem 261:4889

309.

Ahmed N, Babaei‐Jadidi R, Howell SK, Thornalley PJ, Beisswenger PJ (2005) Diabetes Care 28:2465

310.

Glomb MA, Pfahler C (2001) J Biol Chem 276:41638

311.

Glomb MA, Tschirnich R (2001) J Agricult Food Chem 49:5543

312.

Lo TW, Westwood ME, McLellan AC, Selwood T, Thornalley PJ (1994) J Biol Chem 269:32299

313.

Lopez MG, Mancilla‐Margalli NA (2000) Frontiers of Flavour Science. Proceedings of the 9th Weurman Flavour Research Symposium, Freising, Germany, June 22–25

314.

Li EY, Feather MS (1994) Carbohydr Res 256:41

315.

Nagaraj RH, Monnier VM (1995) Biochim Biophys Acta 1253:75

316.

Nagaraj RH, Sady C (1996) FEBS Lett 382:234

317.

Nagaraj RH, Sarkar P, Mally A, Biemel KM, Lederer MO, Padayatti PS (2002) Arch Biochem Biophys 402:110

318.

Pischetsrieder M, Larisch B, Seidel W (1997) J Agric Food Chem 45:2070

319.

Dyer DG, Blackledge JA, Katz BM, Hull CJ, Adkisson HD, Thorpe SR, Lyons TJ, Baynes JW (1991) Z Ernahrungswiss 30:29

320.

Dyer DG, Blackledge JA, Thorpe SR, Baynes JW (1991) J Biol Chem 266:11654

321.

Smith PR, Somani HH, Thornalley PJ, Benn J, Sonksen PH (1993) Clin Sci (Lond) 84:87

322.

Smith PR, Thornalley PJ (1992) Eur J Biochem 210:729

323.

Nissimov J, Elchalal U, Bakala H, Brownlee M, Berry E, Phillip M, Milner Y (2007) J Immunolog Method 320:1

324.

Meerwaldt R, Lutgers HL, Links TP, Graaff R, Baynes JW, Gans ROB, Smit AJ (2007) Diabetes Care 30:107

325.

Yu Y, Thorpe SR, Jenkins AJ, Shaw JN, Sochaski MA, Mcgee D, Aston CE, Orchard TJ, Silvers N, Peng YG, McKnight JA, Baynes JW, Lyons TJ, Grp DER (2006) Diabetologia 49:2488

326.

Lutgers HL, Graaff R, Links TP, Ubink-Veltmaat LJ, Bilo HJ, Gans RO, Smit AJ (2006) Diabetes Care 29:2654

327.

Stitt AW, Jenkins AJ, Cooper ME (2002) Expert Opin Inv Drug 11:1205

328.

Raj DSC, Choudhury D, Welbourne TC, Levi M (2000) Am J Kidney Dis 35:365

329.

Chiarelli F, Catino M, Tumini S, Cipollone F, Mezzetti A, Vanelli M, Verrotti A (2000) Pediatr Nephrol 14:841

330.

DeGroot J (2004) Curr Opin Pharmacol 4:301

331.

Chellan P, Nagaraj RH (2001) J Biol Chem 276:3895

332.

Biemel KM, Reihl O, Conrad J, Lederer MO (2001) J Biol Chem 276:23405

Titel: Degradations and Rearrangement Reactions
verfasst von: Jianbo Zhang
Verlag: Springer Berlin Heidelberg
Buch: Glycoscience
Print ISBN: 978-3-540-36154-1

Electronic ISBN: 978-3-540-30429-6

Copyright-Jahr: 2008
DOI: https://doi.org/10.1007/978-3-540-30429-6_9