Standard Article

Cyclobutane Pyrimidine Dimers as UV-Induced DNA Lesions

Cyclobutanes (2005)

  1. Marcus G. Friedel,
  2. Johannes Gierlich,
  3. Thomas Carell

Published Online: 15 DEC 2009

DOI: 10.1002/9780470682531.pat0336

Patai's Chemistry of Functional Groups

Patai's Chemistry of Functional Groups

How to Cite

Friedel, M. G., Gierlich, J. and Carell, T. 2009. Cyclobutane Pyrimidine Dimers as UV-Induced DNA Lesions. Patai's Chemistry of Functional Groups. .

Author Information

  1. LMU München, Department of Chemistry, München, Germany

Publication History

  1. Published Online: 15 DEC 2009

Chemistry Terms

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Abstract

  • 1
    Introduction
  • 2
    Synthesis of Uracil and Thymine CPDS as the Basis for the Development of Model Compounds
  • 3
    CPD Cleavage Investigations
  • 4
    Investigations with Covalently Linked Model Compounds
  • 5
    Synthesis of Uracil and Thymine CPD Phosphoramidite Building Blocks111
  • 6
    CPD Lesions Embedded in DNA
  • 7
    Acknowledgment

Keywords:

  • cyclobutane pyrimidine dimers (CPD);
  • pyrimidines yielding direct irradiation;
  • C3-linked cytosine CPD compound synthesis;
  • Cis-syn dimer recognizing receptors;
  • CPD cleavage investigations;
  • cyclobutane pyrimidine dimer radical anions;
  • covalently linked model compounds;
  • triplet-sensitized irradiation

Featured Compounds

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  1. 1 - 80
Compound 2
Molecular Weight:126.1133
Molecular Formula:C5H6N2O2
InChIKey:RWQNBRDOKXIBIV-UHFFFAOYSA-N
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Compound 1
Molecular Weight:112.0868
Molecular Formula:C4H4N2O2
InChIKey:ISAKRJDGNUQOIC-UHFFFAOYSA-N
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Compound 3
Molecular Weight:224.1735
Molecular Formula:C8H8N4O4
InChIKey:XFDCFFIAUVAAFU-GNSDDBTRSA-N
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Compound 4
Molecular Weight:252.2267
Molecular Formula:C10H12N4O4
InChIKey:ASJWEHCPLGMOJE-LJMGSBPFSA-N
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Compound 7
Molecular Weight:224.1735
Molecular Formula:C8H8N4O4
InChIKey:XFDCFFIAUVAAFU-ZNIBRBMXSA-N
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Compound 8
Molecular Weight:252.2267
Molecular Formula:C10H12N4O4
InChIKey:ASJWEHCPLGMOJE-ZCZDTUGYSA-N
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Compound 5
Molecular Weight:224.1735
Molecular Formula:C8H8N4O4
InChIKey:LRFJERMEBKCIKN-KXMYSMCESA-N
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Compound 6
Molecular Weight:252.2267
Molecular Formula:C10H12N4O4
InChIKey:PVUJRIKJHMXMHU-VZHHJLAPSA-N
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Compound 9
Molecular Weight:224.1735
Molecular Formula:C8H8N4O4
InChIKey:LRFJERMEBKCIKN-NXWJNSQMSA-N
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Compound 10
Molecular Weight:252.2267
Molecular Formula:C10H12N4O4
InChIKey:PVUJRIKJHMXMHU-WMAJIREVSA-N
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Compound 11
Molecular Weight:256.449
Molecular Formula:C10H20N2O2Si2
InChIKey:FSBNTQRWSOTNEW-UHFFFAOYSA-N
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Compound 12
Molecular Weight:270.4756
Molecular Formula:C11H22N2O2Si2
InChIKey:DRNUNECHVNIYHQ-UHFFFAOYSA-N
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Compound 15
Molecular Weight:264.2374
Molecular Formula:C11H12N4O4
InChIKey:MCMWGSKKIBQHNB-UHFFFAOYSA-N
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Compound 16
Molecular Weight:292.2905
Molecular Formula:C13H16N4O4
InChIKey:BMRBWWWZFYXCDX-UHFFFAOYSA-N
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Compound 13
Molecular Weight:233.063
Molecular Formula:C7H9BrN2O2
InChIKey:BBBZEPSNPDZFIZ-UHFFFAOYSA-N
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Compound 14
Molecular Weight:247.089
Molecular Formula:C8H11BrN2O2
InChIKey:PKTVBCNBVGNGLG-UHFFFAOYSA-N
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Compound 17
Molecular Weight:264.2374
Molecular Formula:C11H12N4O4
InChIKey:BQIYJXWMYXBYBW-DPTVFECHSA-N
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Compound 18
Molecular Weight:292.2905
Molecular Formula:C13H16N4O4
InChIKey:RIQXVIINDMCVKR-HUBGNOAJSA-N
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Compound 19
Molecular Weight:394.4238
Molecular Formula:C21H22N4O4
InChIKey:QAHOPXNZIWMDKI-DIYOSNLNSA-N
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Compound 20
Molecular Weight:296.369
Molecular Formula:C11H12N4O2S2
InChIKey:VDUQIGRQHJKPCE-UHFFFAOYSA-N
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Compound 21
Molecular Weight:318.3742
Molecular Formula:C15H22N6O2
InChIKey:KMMJOHNDEIIPER-UHFFFAOYSA-N
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Compound 22
Molecular Weight:318.3742
Molecular Formula:C15H22N6O2
InChIKey:PFZQSYXTVRNWTL-UHFFFAOYSA-N
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Compound 23
Molecular Weight:524.521
Molecular Formula:C23H32N4O10
InChIKey:MVEYNMKHNLWNDD-GRUVHVDGSA-N
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Compound 24
Molecular Weight:292.2905
Molecular Formula:C13H16N4O4
InChIKey:OSEHFNPYRHDOCK-UHFFFAOYSA-N
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Compound 25
Molecular Weight:292.2905
Molecular Formula:C13H16N4O4
InChIKey:UGUFJGLYRAPMTK-HUBGNOAJSA-N
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Compound 26
Molecular Weight:140.1399
Molecular Formula:C6H8N2O2
InChIKey:GKMIDMKPBOUSBQ-UHFFFAOYSA-N
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Compound 27
Molecular Weight:228.675
Molecular Formula:C10H13ClN2O2
InChIKey:VQXIWTPVIDVUGZ-ONEGZZNKSA-N
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Compound 28
Molecular Weight:332.3544
Molecular Formula:C16H20N4O4
InChIKey:HUTKIGCXBWVICA-AATRIKPKSA-N
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Compound 29
Molecular Weight:332.3544
Molecular Formula:C16H20N4O4
InChIKey:NVJXMNMUAXBYNW-GMKKVBNNSA-N
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Compound 30
Molecular Weight:492.162
Molecular Formula:C16H20Br2N4O4
InChIKey:DQCZSLRKSUXQTQ-SVRVAISLSA-N
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Compound 31
Molecular Weight:280.2798
Molecular Formula:C12H16N4O4
InChIKey:BFNWPAJRJMZJNM-KOCIBTFFSA-N
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Compound 32
Molecular Weight:170.1228
Molecular Formula:C6H6N2O4
InChIKey:ZFNQFXDDQAEAFI-UHFFFAOYSA-N
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Compound 33
Molecular Weight:184.1494
Molecular Formula:C7H8N2O4
InChIKey:TZDMCKHDYUDRMB-UHFFFAOYSA-N
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Compound 34
Molecular Weight:366.283
Molecular Formula:C14H14N4O8
InChIKey:PWWHKOIOVOKJIS-UHFFFAOYSA-N
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Compound 35
Molecular Weight:394.3361
Molecular Formula:C16H18N4O8
InChIKey:DYNWMQRJLNXLPB-UHFFFAOYSA-N
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Compound 36
Molecular Weight:366.283
Molecular Formula:C14H14N4O8
InChIKey:MOUNBXRDQWLRFU-LGUIWLBCSA-N
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Compound 37
Molecular Weight:394.3361
Molecular Formula:C16H18N4O8
InChIKey:QCXGJPCFRKGJQB-QPGDOINGSA-N
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Compound 38
Molecular Weight:340.2457
Molecular Formula:C12H12N4O8
InChIKey:HOLKDBKDGSPVNR-INFAEJQFSA-N
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Compound 39
Molecular Weight:368.2988
Molecular Formula:C14H16N4O8
InChIKey:ODMVFMGBBUCYTA-CDNKIBNWSA-N
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Compound 40
Molecular Weight:260.2454
Molecular Formula:C13H12N2O4
InChIKey:GHQBNJDEIFXXST-UHFFFAOYSA-N
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Compound 41
Molecular Weight:274.272
Molecular Formula:C14H14N2O4
InChIKey:PCHQLPVUECDATJ-UHFFFAOYSA-N
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Compound 42
Molecular Weight:520.4908
Molecular Formula:C26H24N4O8
InChIKey:PHEWWENXZJSIKJ-COPRSSIGSA-N
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Compound 43
Molecular Weight:548.5439
Molecular Formula:C28H28N4O8
InChIKey:OWPXRYLJWAHEAL-OPQYHKBDSA-N
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Compound 44
Molecular Weight:520.4908
Molecular Formula:C26H24N4O8
InChIKey:JSGWNWWEJIVKTN-CBPXPLCBSA-N
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Compound 45
Molecular Weight:548.5439
Molecular Formula:C28H28N4O8
InChIKey:JBNRNTOHHPLESS-BYXJMBFLSA-N
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Compound 46
Molecular Weight:520.4908
Molecular Formula:C26H24N4O8
InChIKey:PHEWWENXZJSIKJ-GXRSIYKFSA-N
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Compound 47
Molecular Weight:548.5439
Molecular Formula:C28H28N4O8
InChIKey:OWPXRYLJWAHEAL-SHRQFBHGSA-N
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Compound 48
Molecular Weight:520.4908
Molecular Formula:C26H24N4O8
InChIKey:JSGWNWWEJIVKTN-URSFVKLHSA-N
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Compound 49
Molecular Weight:548.5439
Molecular Formula:C28H28N4O8
InChIKey:JBNRNTOHHPLESS-RMHFWRJXSA-N
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Compound 50
Molecular Weight:930.9238
Molecular Formula:C44H46N14O10
InChIKey:AYXGUVFQDNTXRC-JSUIZOTQSA-N
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Compound 51
Molecular Weight:958.977
Molecular Formula:C46H50N14O10
InChIKey:UWMKFLLHAUVXJR-QUHLMHKFSA-N
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Compound 52
Molecular Weight:465.4619
Molecular Formula:C22H23N7O5
InChIKey:SYOIRVFUALVYEC-UHFFFAOYSA-N
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Compound 53
Molecular Weight:479.4885
Molecular Formula:C23H25N7O5
InChIKey:XWRMLPQCHLUSQX-UHFFFAOYSA-N
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Compound 54
Molecular Weight:704.7329
Molecular Formula:C33H40N10O8
InChIKey:FWTMCAJWIFJHSI-ALNDXVPUSA-N
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Compound 55
Molecular Weight:691.7071
Molecular Formula:C36H42N3O9P
InChIKey:QZPDEEQLKUHOAL-IYIGGAOFSA-N
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Compound 56
Molecular Weight:356.4894
Molecular Formula:C16H28N2O5Si
InChIKey:QAPSNMNOIOSXSQ-YNEHKIRRSA-N
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Compound 57
Molecular Weight:977.0756
Molecular Formula:C48H61N4O14PSi
InChIKey:DCUDZTVSIZXAEH-UJMMSAFPSA-N
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Compound 58
Molecular Weight:674.7092
Molecular Formula:C27H43N4O12PSi
InChIKey:CXGSCNDEJXVMAD-RCYQMQQRSA-N
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Compound 59
Molecular Weight:674.7092
Molecular Formula:C27H43N4O12PSi
InChIKey:NHHKBEHHHFHVNX-ZTFCDIRKSA-N
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Compound 60
Molecular Weight:674.7092
Molecular Formula:C27H43N4O12PSi
InChIKey:NHHKBEHHHFHVNX-YWEUKOEDSA-N
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Compound 61
Molecular Weight:977.0756
Molecular Formula:C48H61N4O14PSi
InChIKey:ADRRLTLJRCFQSO-ISAMOYFPSA-N
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Compound 62
Molecular Weight:862.8147
Molecular Formula:C42H47N4O14P
InChIKey:OWIFYHOIKRVENR-UTDKWPLASA-N
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Compound 63
Molecular Weight:1009.9269
Molecular Formula:C47H57N5O16P2
InChIKey:BUYNIKICVCIBKQ-GKZJIFDDSA-N
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Compound 64
Molecular Weight:744.8128
Molecular Formula:C40H49N4O8P
InChIKey:UNOTXUFIWPRZJX-CEXSRUIHSA-N
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Compound 65
Molecular Weight:340.3285
Molecular Formula:C15H20N2O7
InChIKey:DSXAZYNMJFDPHQ-QJPTWQEYSA-N
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Compound 66
Molecular Weight:999.9507
Molecular Formula:C49H54N5O16P
InChIKey:HKODKZWZXNOIPR-CWZHFCLMSA-N
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Compound 67
Molecular Weight:697.5843
Molecular Formula:C28H36N5O14P
InChIKey:MEWMGRLYLPHSNJ-OSXDQENJSA-N
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Compound 68
Molecular Weight:697.5843
Molecular Formula:C28H36N5O14P
InChIKey:QRGZRFPUAQNVSW-HYPAKBBVSA-N
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Compound 69
Molecular Weight:697.5843
Molecular Formula:C28H36N5O14P
InChIKey:QRGZRFPUAQNVSW-OEVMKVOVSA-N
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Compound 70
Molecular Weight:999.9507
Molecular Formula:C49H54N5O16P
InChIKey:RNQKOJRTHRYHNS-OOSBHVSWSA-N
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Compound 71
Molecular Weight:901.8508
Molecular Formula:C44H48N5O14P
InChIKey:XMKYUTYZQJMULY-MZZZLCOGSA-N
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Compound 72
Molecular Weight:1102.0686
Molecular Formula:C53H65N7O15P2
InChIKey:YFTKYTMKXZXYAZ-FBQPKOOYSA-N
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Compound 73
Molecular Weight:330.357
Molecular Formula:C13H18N2O6S
InChIKey:CQZJIADHXBNABR-HOSYDEDBSA-N
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Compound 74
Molecular Weight:270.2387
Molecular Formula:C11H14N2O6
InChIKey:FGVDVJQZNYYWJO-QXFUBDJGSA-N
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Compound 75
Molecular Weight:552.488
Molecular Formula:C23H28N4O12
InChIKey:GQDJNLGOCFJHBK-CIJYDTQTSA-N
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Compound 76
Molecular Weight:552.488
Molecular Formula:C23H28N4O12
InChIKey:FGEVVPWXXKMFPP-NJFLDOCBSA-N
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Compound 77
Molecular Weight:552.488
Molecular Formula:C23H28N4O12
InChIKey:FGEVVPWXXKMFPP-PTDNPXRZSA-N
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Compound 78
Molecular Weight:552.488
Molecular Formula:C23H28N4O12
InChIKey:FGEVVPWXXKMFPP-PMPOJZARSA-N
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Compound 79
Molecular Weight:468.4147
Molecular Formula:C19H24N4O10
InChIKey:XTZMUBJYHIYPFB-UGYHJQEQSA-N
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Compound 80
Molecular Weight:970.9989
Molecular Formula:C49H59N6O13P
InChIKey:VYGNDQQRCQPRCI-DSCGRWRXSA-N
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  1. 1 - 80