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Page 1: Supplementary Material A concise synthesis of isoguanine 2

General Papers ARKIVOC 2021, viii, S1-S14

Page S1 ©AUTHOR(S)

Supplementary Material

A concise synthesis of isoguanine 2’-deoxyriboside and its adenine-like triplex formation when incorporated into DNA

Andrew J. Walsh, Carl H. Schwalbe and William Fraser*

College of Health and Life Sciences, Aston University, Aston Triangle, Birmingham, B4 7ET, UK

Email: [email protected]

Table of Contents

Compound 2: 1H NMR (250.1 MHz, CDCl3) S2

Compound 2: 13C NMR (62.9 MHz, CDCl3) S2

Compounds 3 and 4: 1H NMR (250.1 MHz, CDCl3) S3

Compound 5: 1H NMR (250.1 MHz, (CD3)2SO) S4

Compound 5: 13C NMR (62.9 MHz, (CD3)2SO) S4

Compound 6: 1H NMR (250.1 MHz, (CD3)2SO) S5

Compound 6: 13C NMR (62.9 MHz, (CD3)2SO) S5

Compound 7: 1H NMR (250.1 MHz, (CD3)2SO) S6

Compound 7: 13C NMR (62.9 MHz, (CD3)2SO) S6

Compound 8: 1H NMR (250.1 MHz, (CD3)2SO) S7

Compound 8: 13C NMR (62.9 MHz, (CD3)2SO) S7

Compound 9: 1H NMR (250.1 MHz, (CD3)2SO) S8

Compound 9: 13C NMR (62.9 MHz, (CD3)2SO) S8

Compound 11: 1H NMR (250.1 MHz, (CD3)2SO) S9

Compound 11: 13C NMR (62.9 MHz, (CD3)2SO) S9

Compound 13: 1H NMR (250.1 MHz, (CD3)2SO) S10

Compound 13: 13C NMR (62.9 MHz, (CD3)2SO) S10

Compound 14: 1H NMR (250.1 MHz, (CD3)2SO) S11

Compound 14: 13C NMR (62.9 MHz, (CD3)2SO) S11

Compound 14: 31P NMR (101.3 MHz, (CD3)2SO) S12

Compound 15: 1H NMR (250.1 MHz, (CD3)2SO) S13

Compound 15: 13C NMR (62.9 MHz, (CD3)2SO) S13

Compound 15: 31P NMR (101.3 MHz, (CD3)2SO) S14

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Page 2: Supplementary Material A concise synthesis of isoguanine 2

General Papers ARKIVOC 2021, viii, S1-S14

Page S2 ©AUTHOR(S)

Compound 2: 1H NMR (250.1 MHz, CDCl3)

Compound 2: 13C NMR (62.9 MHz, CDCl3)

Page 3: Supplementary Material A concise synthesis of isoguanine 2

General Papers ARKIVOC 2021, viii, S1-S14

Page S3 ©AUTHOR(S)

Compounds 3 and 4: 1H NMR (250.1 MHz, (CDCl3)

Page 4: Supplementary Material A concise synthesis of isoguanine 2

General Papers ARKIVOC 2021, viii, S1-S14

Page S4 ©AUTHOR(S)

Compound 5: 1H NMR (250.1 MHz, (CD3)2SO)

Compound 5: 13C NMR (62.9 MHz, (CD3)2SO)

Page 5: Supplementary Material A concise synthesis of isoguanine 2

General Papers ARKIVOC 2021, viii, S1-S14

Page S5 ©AUTHOR(S)

Compound 6: 1H NMR (250.1 MHz, (CD3)2SO)

Compound 6: 13C NMR (62.9 MHz, (CD3)2SO)

Page 6: Supplementary Material A concise synthesis of isoguanine 2

General Papers ARKIVOC 2021, viii, S1-S14

Page S6 ©AUTHOR(S)

Compound 7: 1H NMR (250.1 MHz, (CD3)2SO)

Compound 7: 13C NMR (62.9 MHz, (CD3)2SO)

Page 7: Supplementary Material A concise synthesis of isoguanine 2

General Papers ARKIVOC 2021, viii, S1-S14

Page S7 ©AUTHOR(S)

Compound 8: 1H NMR (250.1 MHz, (CD3)2SO)

Compound 8: 13C NMR (62.9 MHz, (CD3)2SO)

Page 8: Supplementary Material A concise synthesis of isoguanine 2

General Papers ARKIVOC 2021, viii, S1-S14

Page S8 ©AUTHOR(S)

Compound 9: 1H NMR (250.1 MHz, (CD3)SO)

Compound 9: 13C NMR (62.9 MHz, (CD3)2SO)

Page 9: Supplementary Material A concise synthesis of isoguanine 2

General Papers ARKIVOC 2021, viii, S1-S14

Page S9 ©AUTHOR(S)

Compound 11: 1H NMR (250.1 MHz, (CD3)2SO)

Compound 11: 13C NMR (62.9 MHz, (CD3)2SO)

Page 10: Supplementary Material A concise synthesis of isoguanine 2

General Papers ARKIVOC 2021, viii, S1-S14

Page S10 ©AUTHOR(S)

Compound 13: 1H NMR (250.1 MHz, (CD3)2SO)

Compound 13: 13C NMR (62.9 MHz, (CD3)2SO)

Page 11: Supplementary Material A concise synthesis of isoguanine 2

General Papers ARKIVOC 2021, viii, S1-S14

Page S11 ©AUTHOR(S)

Compound 14: 1H NMR (250.1 MHz, (CD3)2SO)

Compound 14: 13C NMR (62.9 MHz, (CD3)2SO)

Page 12: Supplementary Material A concise synthesis of isoguanine 2

General Papers ARKIVOC 2021, viii, S1-S14

Page S12 ©AUTHOR(S)

Compound 14: 31P NMR (101.3 MHz, (CD3)2SO)

Page 13: Supplementary Material A concise synthesis of isoguanine 2

General Papers ARKIVOC 2021, viii, S1-S14

Page S13 ©AUTHOR(S)

Compound 15: 1H NMR (250.1 MHz, (CD3)2SO)

Compound 15: 13C NMR (62.9 MHz, (CD3)2SO)

Page 14: Supplementary Material A concise synthesis of isoguanine 2

General Papers ARKIVOC 2021, viii, S1-S14

Page S14 ©AUTHOR(S)

Compound 15: 31P NMR (101.3 MHz, (CD3)2SO)


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