Knowledge (XXG)

Reichstein process

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Though many organisms synthesize their own vitamin C, the steps can be different in plants and mammals. Smirnoff concluded that “..little is known about many of the enzymes involved in ascorbate biosynthesis or about the factors controlling flux through the pathways". There is interest in finding
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Even today industrial methods for the production of ascorbic acid can be based on the Reichstein process. In modern methods however, sorbose is directly oxidized with a platinum catalyst (developed by
253:. Glucose is converted to 2-keto-L-gulonic acid in two steps (via 2,4-diketo-L-gulonic acid intermediate) as compared to five steps in the traditional process. 242:(1908–2005) in 1942). This method avoids the use of protective groups. A side product with particular modification is 5-Keto-D-gluconic acid. 282: 257:
alternatives to the Reichstein process. Experiments suggest that genetically modified bacteria might be commercially usable.
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Direct oxidation of L-sorbose to 2-Keto-L-gulonic acid with molecular oxygen on Platinum- and Palladium-based catalysts
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The microbial oxidation of sorbitol to sorbose is important because it provides the correct
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A shorter biotechnological synthesis of ascorbic acid was announced in 1988 by
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in 1934. The first commercially sold vitamin C product was either
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and his colleagues in 1933 while working in the laboratory of the
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Harold A. Wittcoff, Bryan G. Reuben, Jeffery S. Plotkin (2012).
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that takes place in several steps. This process was devised by
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Microbial processes for ascorbic acid biosynthesis: a review
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to Diacetone-L-sorbose (2,3:4,6−Diisopropyliden−α−L−sorbose)
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Biotechnological approaches for L-ascorbic acid production
277:. S. Hirzel Verlag Stuttgart; 24. überarb Auflage 2004, 471:
The use of microorganisms in L-ascorbic acid production
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Eine ergiebige Synthese der L-Ascorbinsäure (C-Vitamin)
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http://www.chemieunterricht.de/dc2/asch2/a-synthe.htm
397:Hancock, Robert D. und Viola, Roberto. (2002): 8: 511:Der Schweizerische Weg zur Viamin-C-Synthese 102:under high temperature and high pressure. 294:Reichstein, T. und Grüssner, A. (1934): 266: 219:This process was patented and sold to 139:groups in sorbose by formation of the 7: 273:Wittko Francke und Wolfgang Walter: 183:can also be prepared directly from 14: 199: 275:Lehrbuch der Organischen Chemie 1: 494:10.1016/j.jbiotec.2006.01.010 422:10.1016/S0167-7799(02)01991-1 379:10.1016/s0083-6729(01)61008-2 35:method for the production of 460:10.1016/0141-0229(90)90159-N 363:L-ascorbic acid biosynthesis 347:Industrial Organic Chemicals 542: 349:. John Wiley & Sons, 235:from Hoffmann-La Roche. 67:The reaction steps are: 442:Enzyme Microb Technol. 403:Trends in Biotechnology 335:10.1006/jcat.1994.1336 247:Genencor International 176:with removal of water. 159:potassium permanganate 436:Boudrant, J. (1990): 367:Vitamins and Hormones 361:Smirnoff, Nicholas. 168:The final step is a 129:4-6 and 30 °C. 49:Tadeusz Reichstein 21:Reichstein process 526:Organic reactions 408:(7); S. 299–305; 329:(1), S. 199–211; 221:Hoffmann-La Roche 170:ring-closing step 155:Organic oxidation 116: 85: 77: 533: 424: 395: 389: 359: 353: 343: 337: 312: 306: 300:Helv. Chim. Acta 292: 286: 271: 251:Eastman Chemical 203: 114: 92:organic reaction 83: 75: 16:Chemical process 541: 540: 536: 535: 534: 532: 531: 530: 516: 515: 502: 433: 428: 427: 396: 392: 360: 356: 344: 340: 314:Brönnimann, C. 313: 309: 293: 289: 272: 268: 263: 217: 209:stereochemistry 163:Diprogulic acid 113:of sorbitol to 65: 17: 12: 11: 5: 539: 537: 529: 528: 518: 517: 514: 513: 508: 501: 500:External links 498: 497: 496: 480:(1); 196–205; 463: 432: 429: 426: 425: 390: 354: 338: 307: 287: 265: 264: 262: 259: 216: 213: 205: 204: 196: 195: 177: 166: 152: 130: 103: 64: 63:Reaction steps 61: 27:is a combined 15: 13: 10: 9: 6: 4: 3: 2: 538: 527: 524: 523: 521: 512: 509: 507: 504: 503: 499: 495: 491: 487: 483: 479: 476: 475:J Biotechnol. 472: 468: 464: 462: 461: 457: 453: 449: 445: 439: 435: 434: 430: 423: 419: 415: 411: 407: 404: 400: 394: 391: 387: 383: 380: 376: 372: 368: 364: 358: 355: 352: 348: 342: 339: 336: 332: 328: 325: 321: 317: 311: 308: 304: 301: 297: 291: 288: 284: 283:3-7776-1221-9 280: 276: 270: 267: 260: 258: 254: 252: 248: 243: 241: 236: 234: 230: 226: 222: 214: 212: 210: 202: 198: 197: 194: 190: 186: 182: 179:Intermediate 178: 175: 174:lactonization 171: 167: 164: 160: 156: 153: 150: 146: 142: 138: 134: 131: 128: 124: 120: 112: 108: 104: 101: 97: 93: 89: 81: 73: 72:hydrogenation 70: 69: 68: 62: 60: 58: 54: 50: 46: 42: 38: 37:ascorbic acid 34: 30: 26: 22: 477: 474: 470: 466: 446:(5); 322–9; 443: 441: 437: 405: 402: 398: 393: 370: 366: 362: 357: 346: 341: 326: 323: 319: 315: 310: 305:, S. 311–328 302: 295: 290: 274: 269: 255: 244: 237: 224: 218: 206: 184: 180: 111:fermentation 66: 20: 18: 465:Bremus, C. 123:acetobacter 45:Nobel Prize 431:Literature 261:References 240:Kurt Heyns 215:Importance 133:protection 105:Microbial 373::241-66. 324:J. Catal. 172:or gamma 135:of the 4 107:oxidation 41:D-glucose 33:microbial 25:chemistry 520:Category 486:16516325 469:(2006): 414:12062975 386:11153268 351:Page 370 318:(1994): 285:; S. 480 193:platinum 137:hydroxyl 100:catalyst 88:sorbitol 29:chemical 452:1366548 233:Redoxon 147:and an 145:acetone 119:sorbose 80:glucose 47:winner 484:  473:. In: 467:et al. 450:  440:. In: 412:  401:. In: 384:  369:2001; 365:. In: 322:. In: 316:et al. 281:  225:Cebion 189:oxygen 141:acetal 96:nickel 57:Zürich 229:Merck 227:from 187:with 157:with 143:with 121:with 98:as a 94:with 90:, an 39:from 482:PMID 448:PMID 410:PMID 382:PMID 279:ISBN 249:and 191:and 161:(to 149:acid 31:and 19:The 490:doi 478:124 456:doi 418:doi 375:doi 331:doi 327:150 231:or 125:at 109:or 82:to 74:of 55:in 53:ETH 23:in 522:: 488:; 454:; 444:12 406:20 371:61 303:17 298:, 211:. 127:pH 59:. 492:: 458:: 420:: 416:; 388:. 377:: 333:: 185:3 181:5 117:- 115:L 86:- 84:D 78:- 76:D

Index

chemistry
chemical
microbial
ascorbic acid
D-glucose
Nobel Prize
Tadeusz Reichstein
ETH
Zürich
hydrogenation
glucose
sorbitol
organic reaction
nickel
catalyst
oxidation
fermentation
sorbose
acetobacter
pH
protection
hydroxyl
acetal
acetone
acid
Organic oxidation
potassium permanganate
Diprogulic acid
ring-closing step
lactonization

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