Paper
RSC Advances
1
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CFA-L-Tyr (11). H-NMR (400 MHz, CD3OD) dH: 7.05 (d, J ¼
8.4 Hz, 2H), 6.69 (d, J ¼ 8.4 Hz, 2H), 6.29 (s, 2H), 4.61 (brs, 1H),
3.19 (dd, J ¼ 13.6, 4.4 Hz, 1H), 3.14–2.90 (m, 2H), 2.37–2.21 (m,
2H), 2.17–2.04 (m, 2H), 1.76 (dt, J ¼ 13.2, 4.8 Hz, 1H), 1.53–1.34
(m, 3H), 1.07 (dt, J ¼ 13.2, 10.8 Hz, 1H), 0.98 (t, J ¼ 7.2 Hz, 3H);
13C-NMR (100 MHz, CD3OD) dc: 222.9, 172.1, 157.3, 138.7, 138.3,
131.4 (2C), 129.6, 116.1 (2C), 84.0, 47.8, 38.7, 38.6, 37.6, 37.3,
29.1, 28.5, 27.2, 11.6; IR (lm) cmꢂ1: 3333, 2964, 2931, 2854,
1733, 1653, 1616, 1516, 1457, 1261, 1226, 1146, 754; HRMS (ESI,
negative) m/z [M ꢂ H]ꢂ calcd for C21H24NO5: 370.1654, found:
370.1658; [a]2D2 +45ꢁ (c 0.10, MeOH).
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1
CFA-L-Gln (12). H-NMR (400 MHz, CD3OD) dH: 6.52 (s, 1H),
4.59 (brs, 1H), 3.18 (dt. J ¼ 10.4, 6.8 Hz, 1H), 2.44–2.28 (m, 6H),
2.26–2.12 (m, 2H), 2.05 (m, 1H) 1.80 (td. J ¼ 12.8, 4.8 Hz, 1H),
1.68–1.35 (m, 3H), 1.14 (td, J ¼ 12.8, 11.2 Hz, 1H), 1.01 (t, J ¼ 7.6
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136.4, 85.0, 47.9, 38.8, 38.7, 37.3, 33.0, 29.1, 29.0, 28.8, 27.1,
11.6; IR (lm) cmꢂ1; 3417, 2961, 2925, 2853, 1733, 1658, 1616,
1532, 1456, 1404, 1263, 1152, 757; HRMS (ESI, negative) m/z [M
ꢂ H]ꢂ calcd for C17H23N2O5: 335.1607, found: 335.1607;
[a]2D2 +52ꢁ (c 0.17, MeOH).
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Alkyne-tagged coronatine (16)
1H-NMR (400 MHz, CD3OD) dH: 7.38 (d, J ¼ 7.6 Hz, 2H), 7.24 (d, J
¼ 7.6 Hz, 2H), 6.28 (s, 1H), 4.70 (dd, J ¼ 10.0, 4.4 Hz, 1H), 3.42 (s,
1H), 3.22–3.02 (m, 3H), 2.36–2.21 (m, 3H), 2.16–2.05 (m, 2H),
1.76 (dt, J ¼ 12.8, 5.2 Hz, 1H), 1.54–1.33 (m, 3H), 1.08 (dt, J ¼
12.8, 11.2 Hz, 1H), 0.98 (t, J ¼ 7.2 Hz, 3H); 13C-NMR (100 MHz,
CD3OD) dc: 222.8, 174.6, 1671.1, 139.9, 138.5, 136.3, 133.1 (2C),
130.4 (2C), 122.3, 84.1, 78.6, 54.9, 47.7, 38.7, 38.5, 37.8, 37.2,
29.0, 28.5, 27.1, 11.6; IR (lm) cmꢂ1: 3292, 2962, 2932, 2875,
2017, 1735, 1655, 1614, 1509, 1444, 1404, 1214, 1148, 1068, 827;
HRMS (ESI, negative) m/z [M ꢂ H]ꢂ calcd for C23H24NO4:
378.1705, found: 378.1705; [a]2D3 +85ꢁ (c 0.10, CHCl3).
Acknowledgements
This work was supported in part by a Grant-in-Aid for Scientic
Research (No. 23102012 to M.U.) on Innovative Areas “Chemical
Biology of Natural Products (No. 2301)”35 from MEXT, Japan;
a Grant-in-Aid for Scientic Research (No. 26282207 to M.U. and
No. 25708026 to Y.T.); a SUNBOR grant (to Y.I.); and a Botanical
Research Grant from the New Technology Development Foun-
dation (to Y.I.). The plasmid of MBP-fused JAZ3 was kindly
gied from Drs A. Chini and R. Solano (CNB, Spain). This
research used computational resources of COMA system
provided by Interdisciplinary Computational Science Program
in Center for Computational Sciences, University of Tsukuba
and Research Center for Computational Science, Okazaki,
Japan.
Notes and references
1 A. Ichihara, K. Shiraishi, H. Sato, S. Sakamura, K. Nishiyama,
R. Sakai, A. Furusaki and T. Matsumoto, J. Am. Chem. Soc., 27 M. Okada, S. Egoshi and M. Ueda, Biosci., Biotechnol.,
1977, 99, 636.
Biochem., 2010, 74, 2092.
This journal is © The Royal Society of Chemistry 2016
RSC Adv., 2016, 6, 19404–19412 | 19411