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Organic & Biomolecular Chemistry
Page 12 of 14
DOI: 10.1039/C6OB00950F
ARTICLE
Journal Name
Moore and S. J. Gange, PLoS One, 2013, 8, e81355/81351-
e81355/81358, 81358 pp.
4. M. Cohen Stacy, M. Gray Kristen, M. C. B. Ocfemia, S. Johnson
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650.
CH2); 1.93 (s, 3H, 14-CH3); 1.78-1.25 (m, 10H, 1′′-CHaHb, 1′′-
CHaHb, 3-CH2, 4-CH2, 2′′-CH2 and 3′′-CH2). 13C NMR (126 MHz,
CD3OD): δ 175.2 (C-1); 173.7 (C-10); 173.4 (C-7); 173.3 (C-13);
158.5 (C-4′); 134.7 (OCH2CH=CH2); 131.1 (C-2′ and C-6′); 129.9
(C-1′); 117.3 (OCH2CH=CH2); 115.5 (C-3′ and C-5′); 69.8
(OCH2CH=CH2); 56.6 (C-11); 54.2 (C-8); 52.3 (OCH3); 40.9 (C-
4′′); 39.8 (C-5); 37.4 (11-CHCH2); 34.2 (C-2); 32.3 (C-2′′); 29.5
(C-3′′); 27.8 (C-4); 23.6 (C-14); 23.0 (C-2′′); 22.8 (C-3).
6. M. Roche, H. Salimi, R. Duncan, B. L. Wilkinson, K. Chikere, M. S.
Moore, N. E. Webb, H. Zappi, J. Sterjovski, J. K. Flynn, A. Ellett, L.
R. Gray, B. Lee, B. Jubb, M. Westby, P. A. Ramsland, S. R. Lewin,
R. J. Payne, M. J. Churchill and P. R. Gorry, Retrovirology, 2013,
10, 43.
7. P. N. Dube, Journal of Chemical, Biological and Physical
Sciences, 2014, 4, 1152-1170, 1119 pp.
8. S. P. Lee, H. G. Kim, M. L. Censullo and M. K. Han, Biochemistry,
1995, 34, 10205-10214.
9. E. Tramontano, P. La Colla and Y.-C. Cheng, Biochemistry, 1998,
37, 7237-7243.
10. Y. Wang, H. Klock, H. Yin, K. Wolff, K. Bieza, K. Niswonger, J.
Matzen, D. Gunderson, J. Hale, S. Lesley, K. Kuhen, J. Caldwell
and A. Brinker, Journal of Biomolecular Screening, 2005, 10,
456-462.
11. A. Mazumder, A. Engelman, R. Craigie, M. Fesen and Y.
Pommier, Nucleic Acids Research, 1994, 22, 1037-1043.
12. A. Mazumder, M. Gupta and Y. Pommier, Nucleic Acids
Research, 1994, 22, 4441-4448.
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and I. Pichova, European Journal of Biochemistry, 2001, 268,
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Pharmacology (San Diego, CA, United States), 2000, 49, 147-
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17. A. S. Espeseth, P. Felock, A. Wolfe, M. Witmer, J. Grobler, N.
Anthony, M. Egbertson, J. Y. Melamed, S. Young, T. Hamill, J. L.
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Sciences of the United States of America, 2000, 97, 11244-
11249.
Methyl (7S,10S)-10-(4-allyloxybenzyl)-7-(4-aminobutyl)-5,8,11-
triaza-12-benzyloxy-6,9,12-trioxododecanoate hydrochloride (96)
Compound 114 (264 mg, 0.33 mmol) was converted to the
uncharacterised N-Fmoc deprotected amine via procedure F,
using 1% piperidine in 9:1 acetonitrile/DMF (10 mL). This was
then converted, via procedure H to the hydrochloride salt 96
(142 mg, 0.23 mmol, 70%) as a hygroscopic brown amorphous
solid. MS (ESI+), m/z 583 (100%) [MH+], 584 (35) [MD+]. HRMS
(ESI+) calcd for C31H42N4O7 + H: 583.3132; found 583.3135.
[α]D25 +176.9 (c. 0.1, EtOH). 1H NMR (300 MHz, CD3OD): δ 8.08
(bs, 1H, NH); 7.56 (bs, 1H, NH); 7.34-7.25 (m, 5H, 2′′′-CH, 3′′′-
CH, 4′′′-CH, 5′′′-CH, 6′′′-CH,); 7.15 (d, J = 7.0 Hz, 2H, 2′-CH and
6′-CH); 6.84 (d, J = 7.0 Hz, 2H, 3′-CH and 5′-CH); 6.14-5.96 (m,
1H, OCH2CH=CH2); 5.38 (bd, J = 17.2 Hz, 1H, OCH2CH=CHH
trans); 5.23 (bd, J = 10.2 Hz, 1H, OCH2CH=CHH cis); 5.09-4.97
(m, 2H, 12-COOCH2); 4.50 (d, J = 4.0 Hz, 2H, OCH2CH=CH2);
4.34-4.24 (m, 2H, 7-CH, 10-CH); 3.64 (s, 3H, OCH3); 3.23-3.11
(m, 2H, 4-CH2); 3.04-2.95 (m, 2H, 4′′-CH2); 2.91-2.82 (m, 2H,
10-CHCH2); 2.36-2.29 (m, 2H, 2-CH2); 1.84-1.60 (m, 6H, 1′′-CH2,
3-CH2 and 3′′-CH2); 1.44-1.30 (m, 2H, 2′′-CH2). 13C NMR (75
MHz, CD3OD): δ 174.2 (C-1); 173.5 (C-9); 173.0 (C-6); 157.9 (C-
4′); 157.3 (C-12); 137.1 (C-1′′′); 134.3 (OCH2CH=CH2); 130.8 (C-
2′ and C-6′); 129.4 (C-1′); 129.0 (C-3′′′ and C-5′′′); 128.4 (C-4′′′);
128.0 (C-2′′′ and C-6′′′); 117.3 (OCH2CH=CH2); 115.2 (C-3′ and
C-5′); 69.7 (OCH2CH=CH); 67.4 (12-COOCH2); 57.4 (C-10); 53.8
(C-7); 52.9 (OCH3); 41.5 (C-4′′); 39.5 (C-4); 37.4 (10-CHCH2);
32.1 (C-1′′); 31.9 (C-2); 27.8 (C-3′′); 25.3 (C-3); 23.6 (C-2′′).
Acknowledgements
CPG is the recipient of an ARC DECRA fellowship and
acknowledges the postgraduate scholarship provided the
University of Wollongong and the ARC Linkage program. ND
acknowledges the University of Wollongong and Avexa for a
matching scholarship.
18. G. Chi, N. Neamati and V. Nair, Bioorganic & Medicinal
Chemistry Letters, 2004, 14, 4815-4817.
19. M. L. Barreca, L. De Luca, N. Iraci and A. Chimirri, Journal of
Medicinal Chemistry, 2006, 49, 3994-3997.
20. C. P. Gordon, R. Griffith and P. A. Keller, Medicinal Chemistry,
2007, 3, 199-220.
21. R. Di Santo, Journal of Medicinal Chemistry, 2014, 57, 539-566.
22. K. Gupta, T. Brady, M. Dyer Benjamin, N. Malani, Y. Hwang, F.
Male, T. Nolte Robert, L. Wang, E. Velthuisen, J. Jeffrey, D. Van
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biological chemistry, 2014, 289, 20477-20488.
23. T. S. Peat, D. I. Rhodes, N. Vandegraaff, G. Le, J. A. Smith, L. J.
Clark, E. D. Jones, J. A. V. Coates, N. Thienthong, J. Newman, O.
Dolezal, R. Mulder, J. H. Ryan, G. P. Savage, C. L. Francis and J. J.
Deadman, PLoS One, 2012, 7, e40147.
Notes and references
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2. J. M. A. Lange and J. Ananworanich, Antiviral Therapy, 2014, 19,
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Newman, J. Martyn, J. A. V. Coates, N. J. Ede, P. Rea and J. J.
Deadman, ChemBioChem, 2011, 12, 2311-2315.
12 | J. Name., 2012, 00, 1-3
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