Organic & Biomolecular Chemistry
Communication
15 J. W. Goodby, V. Görtz, S. J. Cowling, G. Mackenzie,
P. Martin, D. Plusquellec, T. Benvegnu, P. Boullanger,
D. Lafont, Y. Queneau, S. Chambert and J. Fitremann,
Chem. Soc. Rev., 2007, 36, 1971.
Notes and references
1 (a) J. S. Carey, D. Laffan, C. Thomson and M. T. Williams,
Org. Biomol. Chem., 2006, 4, 2337; (b) S. D. Roughley and
A. M. Jordan, J. Med. Chem., 2011, 54, 3451.
16 P. H. Seeberger and D. B. Wertz, Nature, 2007, 446, 1046.
2 (a) J. M. Humphrey and A. R. Chamberlin, Chem. Rev., 17 (a) P. V. Santacroce and A. Basu, Angew. Chem., Int. Ed.,
1997, 97, 2243; (b) J. W. Bode, Curr. Opin. Drug Discovery
Dev., 2006, 9, 765; (c) T. Cupido, J. Tulla-Puche, J. Spengler
2003, 42, 95; (b) P. V. Santacroce and A. Basu,
Glycoconjugate J., 2004, 21, 89.
and F. Albericio, Curr. Opin. Drug Discovery Dev., 2007, 10, 768. 18 F.-L. Yang, K.-F. Hua, Y.-L. Yang, W. Zou, Y.-P. Chen,
3 E. Valeur and M. Bradley, Chem. Soc. Rev., 2009, 38, 606.
4 D. J. C. Constable, P. J. Dunn, J. D. Hayler, G. R. Humphrey,
S.-M. Liang, H.-Y. Hsu and S.-H. Wu, Glycoconjugate J.,
2008, 25, 427.
J. L. Leazer, R. J. Lindermann, K. Lorenz, J. Manley, 19 S. Trombotto, A. Bouchu, G. Descotes and Y. Queneau,
B. A. Pearlman, A. Wells, A. Zaks and T. Y. Zhang, Green
Chem., 2007, 9, 411.
Tetrahedron Lett., 2000, 41, 8273.
20 (a) S. Trombotto, M. Danel, J. Fitremann, A. Bouchu and
Y. Queneau, J. Org. Chem., 2003, 68, 6672; (b) S. Chambert,
A. Doutheau, Y. Queneau, S. J. Cowling, J. W. Goodby and
G. J. Mackenzie, Carbohydr. Chem., 2007, 26, 27;
(c) C. Barsu, R. Cheaib, S. Chambert, Y. Queneau,
O. Maury, D. Cottet, H. Wege, J. Douady, Y. Bretonnière
and C. Andraud, Org. Biomol. Chem., 2010, 8, 142; (d) R. Xu,
F. Ali-Rachedi, N. M. Xavier, S. Chambert, F. Ferkous,
Y. Queneau, S. J. Cowling, E. J. Davis and J. W. Goodby,
Org. Biomol. Chem., 2015, 13, 783.
5 (a) V. R. Pattabiraman and J. W. Bode, Nature, 2011, 480,
471; (b) C. L. Allen and J. M. Williams, J. Chem. Soc. Rev.,
2011, 40, 3405; (c) R. M. Lanigan and T. D. Sheppard,
Eur. J. Org. Chem., 2013, 7453; (d) R. M. de Figueiredo,
J.-S. Suppo and J.-M. Campagne, Chem. Rev., 2016, 116,
12029.
6 M. V. Sergeeva, V. V. Mozhaev, J. O. Rich and
Y. L. Khmelnitsky, Biotechnol. Lett., 2000, 22, 1419.
7 (a) L. Pauling, R. B. Corey and H. R. Branson, Proc. Natl.
Acad. Sci. U. S. A., 1951, 37, 205; (b) J. Aubé, Angew. Chem., 21 (a) J.-I. Tamura, M. Fukuda, J. Tanaka and M. J. Kawa,
Int. Ed., 2012, 51, 3063.
Carbohydr. Chem., 2002, 21, 445; (b) C. Grandjean,
V. Santraine, N. Fardel, A. Polidori, B. Pucci, H. Gras-Masse
and D. Bonnet, Tetrahedron Lett., 2004, 45, 3451;
(c) P. Virta, M. Karskela and H. J. Lönnberg, Org. Chem.,
2006, 71, 1989; (d) Y.-B. Lim, S. Park, E. Lee, H. Jeong,
J.-H. Ryu, M. S. Lee and M. Lee, Biomacromolecules, 2007, 8,
1404; (e) M. Sleiman, A. Varrot, J.-M. Raimundo,
M. Gingras and P. G. Goekjian, Chem. Commun., 2008,
6507; (f) M. Karskela, M. von Usedom, P. Virta and
H. Lönnberg, Eur. J. Org. Chem., 2012, 6594.
8 (a) R. Szostak, S. Shi, G. Meng, R. Lalancette and
M. J. Szostak, Org. Chem., 2016, 81, 8091; (b) E. L. Baker,
M. M. Yamano, Y. Zhou, S. M. Anthony and N. K. Garg,
Nat. Commun., 2016, 7, 11554; (c) J. E. Dander, E. L. Baker
and N. K. Garg, Chem. Sci., 2017, 8, 6433; (d) Y. Liu, S. Shi,
M. Achtenhagen, R. Liu and M. Szostak, Org. Lett., 2017,
19, 1614–1617.
9 (a) S. E. Eldred, D. A. Stone, S. H. Gellman and S. S. Stahl,
J. Am. Chem. Soc., 2003, 125, 3422; (b) J. M. Hoerter,
K. M. Otte, S. H. Gellman, Q. Cui and S. S. Stahl, J. Am. 22 (a) R. Mahrwald, Chem. Commun., 2015, 51, 13868;
Chem. Soc., 2008, 130, 647.
(b) S. Johnson and F. Tanaka, Org. Biomol. Chem., 2016, 14,
10 M. Shi and S.-C. Cui, Synth. Commun., 2005, 35, 2847.
259.
11 (a) S. N. Rao, D. C. Mohan and S. Adimurthy, Org. Lett., 23 (a) B. G. Davis, J. Chem. Soc., Perkin Trans. 1, 1999, 3215;
2013, 15, 1496; (b) X. Yang, L. Fan and Y. Xue, RSC Adv.,
2014, 4, 30108.
12 C. L. Allen, B. N. Atkinson and J. M. J. Williams, Angew.
Chem., Int. Ed., 2012, 51, 1383.
(b) D. P. Gamblin, E. M. Scanlan and B. G. Davis, Chem.
Rev., 2009, 109, 131; (c) L. Latxague, A. Gaubert and
P. Barthelemy, Molecules, 2018, 23, 89.
24 T. B. Nguyen, J. Sorres, M. Q. Tran, L. Ermolenko and A. Al-
Mourabit, Org. Lett., 2012, 14, 3202.
13 (a) S. A. W. Gruner, E. Locardi, E. Lohof and H. Kessler,
Chem. Rev., 2002, 102, 491; (b) G.-Z. Tian, X.-L. Wang, 25 L. Yu, H. Ye, L. Zheng, L. Chen, K. Chu, X. Liu, X. Xu and
J. Hu, X.-B. Wang, X.-Q. Guo and J. Yin, Chin. Chem. Lett.,
2015, 26, 922.
14 (a) A. Dondoni and A. Marra, Chem. Rev., 2000, 100, 4395;
G. Chen, Electrophoresis, 2011, 32, 218.
26 S. N. Rao, D. C. Mohan and S. Adimurthy, Green Chem.,
2014, 16, 4122.
(b) Z. Guo and N. Shao, Med. Res. Rev., 2005, 25, 655; 27 H. A. Moynihan, J. A. Hayes, K. S. Eccles, S. J. Coles and
(c) H. Hojo and Y. Nakahara, Biopolymers, 2007, 88, 308.
S. E. Lawrence, Carbohydr. Res., 2013, 374, 29.
This journal is © The Royal Society of Chemistry 2019
Org. Biomol. Chem., 2019, 17, 9425–9429 | 9429