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Base J

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van Luenen, Henri G.A.M.; Farris, Carol; Jan, Sabrina; Genest, Paul-Andre; Tripathi, Pankaj; Velds, Arno; Kerkhoven, Ron M.; Nieuwland, Marja; Haydock, Andrew; Ramasamy, Gowthaman; Vainio, Saara; Heidebrecht, Tatjana; Perrakis, Anastassis; Pagie, Ludo; van Steensel, Bas; Myler, Peter J.;
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InChI=1S/C11H16N2O8/c14-2-5-6(15)7(16)8(17)10(21-5)20-3-4-1-12-11(19)13-9(4)18/h1,5-8,10,14-17H,2-3H2,(H2,12,13,18,19)/t5-,6-,7+,8-,10-/m1/s1
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InChI=1/C11H16N2O8/c14-2-5-6(15)7(16)8(17)10(21-5)20-3-4-1-12-11(19)13-9(4)18/h1,5-8,10,14-17H,2-3H2,(H2,12,13,18,19)/t5-,6-,7+,8-,10-/m1/s1
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being accompanied by a massive read-through at RNA polymerase II termination sites, which ultimately proves lethal to the cell.
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and was the first hypermodified nucleobase found in eukaryotic DNA; it has since been found in other kinetoplastids, including
188: 408: 324: 605: 54: 36: 600: 456:, Piet; Sabatini, Robert (October 2008). "Base J: Discovery, Biosynthesis, and Possible Functions". 610: 402: 98: 23: 498:"Glucosylated Hydroxymethyluracil, DNA Base J, Prevents Transcriptional Readthrough in Leishmania" 368: 576: 527: 473: 379: 152: 566: 558: 517: 509: 465: 269: 469: 197: 108: 571: 546: 522: 497: 356: 318: 177: 594: 398: 390: 383: 363: 513: 562: 493: 453: 374: 348: 303: 143: 394: 580: 531: 477: 360: 164: 317:
Except where otherwise noted, data are given for materials in their
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Hazelbaker, Dane Z.; Buratowski, Stephen (November 2012).
366:. It was discovered in 1993, in the trypanosome 176: 107: 382:transcription terminator, with its removal in 8: 378:. Within these organisms Base J acts as a 151: 15: 570: 521: 196: 448: 446: 442: 251: 216: 547:"Transcription: Base J Blocks the Way" 470:10.1146/annurev.micro.62.081307.162750 223:Key: SUDBRAWXUGTELR-HPFNVAMJSA-N 7: 233:Key: SUDBRAWXUGTELR-HPFNVAMJBD 167: 254:c1c(c(=O)c(=O)1)CO2((((O2)CO)O)O)O 14: 389:Base J is formed by the initial 287: 281: 22: 321:(at 25 °C , 100 kPa). 80:-Glucosyl-5-hydroxymethyluracil 59:5-({oxy}methyl)pyrimidine-2,4(1 341:-Glucopyranosyloxymethyluracil 293: 275: 1: 458:Annual Review of Microbiology 86:-Glucosyl-hydroxymethyluracil 412:The biosynthesis of base J. 420:: beta-glucosyltranferase; 627: 514:10.1016/j.cell.2012.07.030 401:by an as yet unidentified 563:10.1016/j.cub.2012.10.010 424:: dT (desoxy thymidine); 416:: thymidine hydroxylase; 315: 262: 242: 207: 91: 73: 53: 35: 30: 21: 496:, Piet (August 2012). 433: 411: 55:Systematic IUPAC name 359:including the human 403:glycosyltransferase 397:and the subsequent 347:is a hypermodified 311: g·mol 18: 434: 369:Trypanosoma brucei 325:Infobox references 40:5-pyrimidine-2,4(1 16: 557:(22): R960–R962. 380:RNA polymerase II 340: 333:Chemical compound 331: 330: 133:Interactive image 85: 79: 618: 606:Pyrimidinediones 585: 584: 574: 542: 536: 535: 525: 488: 482: 481: 450: 338: 310: 295: 289: 283: 277: 270:Chemical formula 200: 180: 169: 155: 135: 111: 83: 77: 26: 19: 626: 625: 621: 620: 619: 617: 616: 615: 591: 590: 589: 588: 551:Current Biology 544: 543: 539: 490: 489: 485: 452: 451: 444: 439: 334: 327: 322: 308: 298: 292: 286: 280: 272: 258: 255: 250: 249: 238: 235: 234: 231: 225: 224: 221: 215: 214: 203: 183: 170: 158: 138: 125: 114: 101: 87: 81: 69: 68: 49: 12: 11: 5: 624: 622: 614: 613: 608: 603: 593: 592: 587: 586: 537: 508:(5): 909–921. 483: 464:(1): 235–251. 441: 440: 438: 435: 384:knockout cells 357:kinetoplastids 332: 329: 328: 323: 319:standard state 316: 313: 312: 306: 300: 299: 296: 290: 284: 278: 273: 268: 265: 264: 260: 259: 257: 256: 253: 245: 244: 243: 240: 239: 237: 236: 232: 229: 228: 226: 222: 219: 218: 210: 209: 208: 205: 204: 202: 201: 193: 191: 185: 184: 182: 181: 173: 171: 163: 160: 159: 157: 156: 148: 146: 140: 139: 137: 136: 128: 126: 119: 116: 115: 113: 112: 104: 102: 97: 94: 93: 89: 88: 75: 71: 70: 58: 57: 51: 50: 39: 33: 32: 28: 27: 13: 10: 9: 6: 4: 3: 2: 623: 612: 609: 607: 604: 602: 599: 598: 596: 582: 578: 573: 568: 564: 560: 556: 552: 548: 541: 538: 533: 529: 524: 519: 515: 511: 507: 503: 499: 495: 487: 484: 479: 475: 471: 467: 463: 459: 455: 449: 447: 443: 436: 431: 427: 423: 419: 415: 410: 406: 404: 400: 399:glycosylation 396: 392: 391:hydroxylation 387: 385: 381: 377: 376: 371: 370: 365: 362: 358: 354: 351:found in the 350: 346: 342: 326: 320: 314: 307: 305: 302: 301: 274: 271: 267: 266: 261: 252: 248: 241: 227: 217: 213: 206: 199: 195: 194: 192: 190: 187: 186: 179: 175: 174: 172: 166: 162: 161: 154: 150: 149: 147: 145: 142: 141: 134: 130: 129: 127: 123: 118: 117: 110: 106: 105: 103: 100: 96: 95: 90: 72: 66: 62: 56: 52: 47: 43: 38: 34: 29: 25: 20: 554: 550: 540: 505: 501: 486: 461: 457: 429: 425: 421: 417: 413: 388: 373: 367: 364:trypanosomes 344: 336: 335: 92:Identifiers 74:Other names 64: 60: 45: 41: 601:Nucleobases 428:: HOCH3dU; 263:Properties 611:Glucosides 595:Categories 437:References 375:Leishmania 361:pathogenic 349:nucleobase 304:Molar mass 198:979DWB8FWS 144:ChemSpider 120:3D model ( 109:53910-89-7 99:CAS Number 37:IUPAC name 395:thymidine 178:129852278 581:23174300 532:22939620 478:18729733 153:32742278 572:3648658 523:3684241 309:304.255 165:PubChem 67:)-dione 48:)-dione 17:Base J 579:  569:  530:  520:  476:  345:base J 247:SMILES 31:Names 494:Borst 454:Borst 212:InChI 122:JSmol 577:PMID 528:PMID 502:Cell 474:PMID 432:: dJ 189:UNII 567:PMC 559:doi 518:PMC 510:doi 506:150 466:doi 393:of 355:of 353:DNA 343:or 168:CID 597:: 575:. 565:. 555:22 553:. 549:. 526:. 516:. 504:. 500:. 472:. 462:62 460:. 445:^ 405:. 337:β- 285:16 279:11 82:β- 76:β- 63:,3 44:,3 583:. 561:: 534:. 512:: 480:. 468:: 430:3 426:2 422:1 418:B 414:A 339:D 297:8 294:O 291:2 288:N 282:H 276:C 124:) 84:D 78:D 65:H 61:H 46:H 42:H

Index


IUPAC name
Systematic IUPAC name
CAS Number
53910-89-7
JSmol
Interactive image
ChemSpider
32742278
PubChem
129852278
UNII
979DWB8FWS
InChI
SMILES
Chemical formula
Molar mass
standard state
Infobox references
nucleobase
DNA
kinetoplastids
pathogenic
trypanosomes
Trypanosoma brucei
Leishmania
RNA polymerase II
knockout cells
hydroxylation
thymidine

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