Knowledge

Keto acid

Source 📝

38: 387:
Hopper, Christopher P.; De La Cruz, Ladie Kimberly; Lyles, Kristin V.; Wareham, Lauren K.; Gilbert, Jack A.; Eichenbaum, Zehava; Magierowski, Marcin; Poole, Robert K.; Wollborn, Jakob; Wang, Binghe (2020-12-23).
344:
Penteado, Filipe; Lopes, Eric F.; Alves, Diego; Perin, Gelson; Jacob, Raquel G.; Lenardão, Eder J. (16 April 2019). "α-Keto Acids: Acylating Agents in Organic Synthesis".
470:
Hewitson, K.S.; McNeill, L.A.; Elkins, J.M.; Schofield, C.J. (1 June 2003). "The role of iron and 2-oxoglutarate oxygenases in signalling".
310:
Franz Dietrich Klingler, Wolfgang Ebertz "Oxocarboxylic Acids" in Ullmann's Encyclopedia of Industrial Chemistry 2005, Wiley-VCH, Weinheim.
96:). In several cases, the keto group is hydrated. The alpha-keto acids are especially important in biology as they are involved in the 526: 144: 331: 205:
Gamma-keto acids, Gamma-ketoacids, or 4-oxoacids have the ketone group at the third carbon from the carboxylic acid.
213:
Keto acids appear in a wide variety of anabolic pathways in metabolism. For instance, in plants (specifically, in
326:
Nelson, D. L.; Cox, M. M. "Lehninger, Principles of Biochemistry" 3rd Ed. Worth Publishing: New York, 2000.
140: 548: 506: 588: 17: 194:, have the ketone group at the second carbon from the carboxylic acid. They generally form by the 97: 166: 248: 124: 116: 198:. The presence of the keto group at the beta position allows them to easily undergo thermal 37: 275: 264: 195: 8: 604: 518: 425: 369: 132: 584: 247:
levels are low, stored fats and proteins are the primary source of energy production.
564: 522: 487: 429: 417: 409: 373: 361: 327: 222: 160: 57: 556: 514: 479: 452: 401: 353: 311: 214: 191: 156: 77: 45: 225:), 5-oxo-octanoic acid is converted in enzymatic and non-enzymatic steps into the 226: 199: 136: 81: 443:
Kerber, Robert C.; Fernando, Marian S. (October 2010). "α-Oxocarboxylic Acids".
405: 357: 206: 182: 174: 49: 389: 598: 568: 413: 315: 287: 268: 256: 218: 170: 491: 421: 365: 244: 150: 41: 560: 115:
have the keto group adjacent to the carboxylic acid. They often arise by
483: 292: 120: 101: 456: 274:
Alpha keto acids are used primarily as energy for liver cells and in
128: 252: 233: 178: 260: 230: 31: 127:
to the same. Alpha-keto acids possesses extensive chemistry as
89: 549:"5-Oxo-octanoic acid and 5-oxo-octanal, precursors of coniine" 469: 390:"Role of Carbon Monoxide in Host–Gut Microbiome Communication" 240: 386: 553:
Journal of the Chemical Society D: Chemical Communications
190:
Beta-keto acids, beta-ketoacids, or 3-oxoacids, such as
343: 27:
Organic compounds with a –COOH group and a C=O group
267:can be deaminated to produce alpha keto acids and 596: 442: 131:agents. Furthermore, alpha-keto acids such as 546: 587:at the U.S. National Library of Medicine 36: 153:, pervasive intermediate in metabolism. 14: 597: 304: 173:. Alpha-ketoglutarate participates in 111:Alpha-keto acids, alpha-ketoacids, or 507:"Functional Group Exchange Reactions" 504: 147:scaffold. Important representatives: 107:Common types of keto acids include: 169:, a 5-carbon ketoacid derived from 24: 519:10.1016/b978-0-12-800720-4.00003-9 25: 616: 578: 547:Leete, E.; Olson, J. O. (1970). 472:Biochemical Society Transactions 540: 498: 463: 436: 380: 337: 320: 13: 1: 445:Journal of Chemical Education 298: 123:, and reciprocally, they are 7: 406:10.1021/acs.chemrev.0c00586 358:10.1021/acs.chemrev.8b00782 281: 135:are endogenous sources for 10: 621: 505:Smith, Michael B. (2017), 29: 513:, Elsevier, p. 137, 181:. It is commonly used in 589:Medical Subject Headings 316:10.1002/14356007.a18_313 30:Not to be confused with 167:alpha-ketoglutaric acid 98:Krebs citric acid cycle 249:Glucogenic amino acids 53: 278:, also in the liver. 265:Ketogenic amino acids 251:from proteins and/or 159:, a component of the 143:) and pharmaceutical 117:oxidative deamination 40: 561:10.1039/C29700001651 276:fatty acid synthesis 196:Claisen condensation 177:by functioning as a 400:(24): 13273–13311. 484:10.1042/bst0310510 133:phenylpyruvic acid 54: 555:(23): 1651–1652. 528:978-0-12-800720-4 511:Organic Synthesis 457:10.1021/ed1003096 451:(10): 1079–1084. 352:(12): 7113–7278. 259:are converted to 78:organic compounds 58:organic chemistry 16:(Redirected from 612: 573: 572: 544: 538: 537: 536: 535: 502: 496: 495: 467: 461: 460: 440: 434: 433: 394:Chemical Reviews 384: 378: 377: 346:Chemical Reviews 341: 335: 324: 318: 308: 192:acetoacetic acid 157:oxaloacetic acid 95: 87: 46:acetoacetic acid 21: 620: 619: 615: 614: 613: 611: 610: 609: 595: 594: 581: 576: 545: 541: 533: 531: 529: 503: 499: 468: 464: 441: 437: 385: 381: 342: 338: 325: 321: 309: 305: 301: 284: 200:decarboxylation 141:gasotransmitter 137:carbon monoxide 93: 85: 82:carboxylic acid 80:that contain a 35: 28: 23: 22: 15: 12: 11: 5: 618: 608: 607: 593: 592: 580: 579:External links 577: 575: 574: 539: 527: 497: 478:(3): 510–515. 462: 435: 379: 336: 319: 302: 300: 297: 296: 295: 290: 288:Ulosonic acids 283: 280: 239:When ingested 223:fool's parsley 219:pitcher plants 211: 210: 209:is an example. 207:Levulinic acid 203: 188: 187: 186: 183:transamination 175:cell signaling 164: 154: 50:levulinic acid 26: 9: 6: 4: 3: 2: 617: 606: 603: 602: 600: 590: 586: 583: 582: 570: 566: 562: 558: 554: 550: 543: 530: 524: 520: 516: 512: 508: 501: 493: 489: 485: 481: 477: 473: 466: 458: 454: 450: 446: 439: 431: 427: 423: 419: 415: 411: 407: 403: 399: 395: 391: 383: 375: 371: 367: 363: 359: 355: 351: 347: 340: 333: 332:1-57259-153-6 329: 323: 317: 313: 307: 303: 294: 291: 289: 286: 285: 279: 277: 272: 270: 269:ketone bodies 266: 262: 258: 257:Triglycerides 254: 250: 246: 242: 237: 235: 232: 228: 224: 220: 216: 208: 204: 201: 197: 193: 189: 184: 180: 176: 172: 171:glutamic acid 168: 165: 162: 158: 155: 152: 149: 148: 146: 142: 138: 134: 130: 126: 122: 118: 114: 110: 109: 108: 105: 103: 99: 91: 83: 79: 75: 71: 68:(also called 67: 63: 59: 51: 47: 43: 39: 33: 19: 552: 542: 532:, retrieved 510: 500: 475: 471: 465: 448: 444: 438: 397: 393: 382: 349: 345: 339: 322: 306: 273: 245:carbohydrate 238: 212: 151:pyruvic acid 112: 106: 73: 69: 65: 61: 55: 42:Pyruvic acid 161:Krebs cycle 121:amino acids 605:Keto acids 585:Keto+Acids 534:2022-06-01 299:References 293:Pseudoacid 185:reactions. 125:precursors 113:2-oxoacids 102:glycolysis 62:keto acids 569:0577-6171 430:224824871 414:0009-2665 374:119535331 234:alkaloids 229:class of 129:acylation 70:oxo acids 66:ketoacids 599:Category 492:12773146 422:33089988 366:30990680 282:See also 253:Glycerol 179:coenzyme 88:) and a 74:oxoacids 52:(bottom) 18:Ketoacid 261:glucose 231:coniine 215:hemlock 145:prodrug 100:and in 94:>C=O 92:group ( 84:group ( 44:(top), 32:oxyacid 591:(MeSH) 567:  525:  490:  428:  420:  412:  372:  364:  330:  241:sugars 227:cyclic 221:, and 139:(as a 90:ketone 76:) are 426:S2CID 370:S2CID 255:from 86:−COOH 565:ISSN 523:ISBN 488:PMID 418:PMID 410:ISSN 362:PMID 328:ISBN 243:and 48:and 557:doi 515:doi 480:doi 453:doi 402:doi 398:120 354:doi 350:119 312:doi 119:of 72:or 64:or 56:In 601:: 563:. 551:. 521:, 509:, 486:. 476:31 474:. 449:87 447:. 424:. 416:. 408:. 396:. 392:. 368:. 360:. 348:. 271:. 263:. 236:. 217:, 104:. 60:, 571:. 559:: 517:: 494:. 482:: 459:. 455:: 432:. 404:: 376:. 356:: 334:. 314:: 202:. 163:. 34:. 20:)

Index

Ketoacid
oxyacid

Pyruvic acid
acetoacetic acid
levulinic acid
organic chemistry
organic compounds
carboxylic acid
ketone
Krebs citric acid cycle
glycolysis
oxidative deamination
amino acids
precursors
acylation
phenylpyruvic acid
carbon monoxide
gasotransmitter
prodrug
pyruvic acid
oxaloacetic acid
Krebs cycle
alpha-ketoglutaric acid
glutamic acid
cell signaling
coenzyme
transamination
acetoacetic acid
Claisen condensation

Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.