Page 9 of 10
ACKNOWLEDGMENT
Journal of the American Chemical Society
sides, G. M. J. Org. Chem. 1993, 58, 7937−7938. (c) Chan, T. H.;
1
2
3
4
5
6
7
8
9
1
1
1
1
1
1
1
1
1
1
2
2
2
2
2
2
2
2
2
2
3
3
3
3
3
3
3
3
3
3
4
4
4
4
4
4
4
4
4
4
5
5
5
5
5
5
5
5
5
5
6
Lee, M. C. J. Org. Chem. 1995, 60, 4228−4232. (d) Choi, S.ꢀK.; Lee,
S.; Whitesides, G. M. J. Org. Chem. 1996, 61, 8739−8745. (e) Gao, J.;
Martichonok, V.; Whitesides, G. M. J. Org. Chem. 1996, 61,
This work was supported by the General Research Fund
17305615, 702813P) of the Research Grants Council of Hong
Kong, the National Natural Science Foundation of China
(21672180), the Area of Excellence Scheme of the University
Grants Committee of Hong Kong (Grant AoE/Pꢀ705/16) and
Shenzhen Basic Research Grant (JCYJ20140903112959961).
(
9
538−9540.
28) Heckendorn, R.; Allgeier, H.; Baud, J.; Gunzenhauser, W.;
Angst, C. J. Med. Chem. 1993, 36, 3721−3726.
29) Fukuyama, T.; Lin, S. C.; Li, L. J. Am. Chem. Soc. 1990, 112,
(
(
7050−7051.
REFERENCES
(30) Kimura, M.; Seki, M. Tetrahedron Lett. 2004, 45, 3219−3223.
(31) The configuration was elucidated via comparison of the H NMR
1
(
(
1) Schäffer, C.; Messner, P. FEMS Microbiol. Rev. 2017, 41, 49−91.
2) Iwashkiw, J. A.; Vozza, N. F.; Kinsella, R. L.; Feldman, M. F.
of 19 with the Barbier adducts reported in ref. 22.
(32) Steurer, S.; Podlech, J. Adv. Synth. Catal. 2001, 343, 251−254.
(33) Sheehan, J. C.; Yang, D. D. H. J. Am. Chem. Soc. 1958, 80,
1154−1158.
(34) (a) Huang, C. Y.; Wang, N.; Fujiki, K.; Otsuka, Y.; Akamatsu,
M.; Fujimoto, Y.; Fukase, K. J. Carbohydr. Chem. 2010, 29,
289−298. For the putative carbamoyl fluoride intermediate in the
deprotection, see: (b) Jacquemard, U.; Bénéteau, V.; Lefoix, M.;
Routier, S.; Mérour, J. Y.; Coudert, G. Tetrahedron 2004, 60,
10039−10047.
(35) (a) Tamura, J.; Yamaguchi, A.; Tanaka, J.; Nishimura, Y. J.
Carbohydr. Chem. 2007, 26, 61−82. (b) Yoshida, K.; Yang, B.; Yang,
W.; Zhang, Z.; Zhang, J.; Huang, X. Angew. Chem. Int. Ed. 2014, 53,
9051−9058.
(36) Gagarinov, I. A.; Fang, T.; Liu, L.; Srivastava, A. D.; Boons, G.ꢀ
J. Org. Lett. 2015, 17, 928−931.
0
1
2
3
4
5
6
7
8
9
0
1
2
3
4
5
6
7
8
9
0
1
2
3
4
5
6
7
8
9
0
1
2
3
4
5
6
7
8
9
0
1
2
3
4
5
6
7
8
9
0
Mol. Microbiol. 2013, 89, 14−28.
3) Nothaft, H.; Szymanski, C. M. Nat. Rev. Microbiol. 2010, 8,
65−778.
4) AbuꢀQarn, M.; Eichler, J.; Sharon, N. Curr. Opin. Struct. Biol.
2008, 18, 544−550.
5) Knirel, Y. A.; Vinogradov, E. V.; L'vov, V. L.; Kocharova, N. A.;
Shashkov, A. S.; Dmitriev, B. A.; Kochetkov, N. K. Carbohydr. Res.
984, 133, C5−C8.
6) (a) Zunk, M.; Kiefel, M. J. RSC Adv. 2014, 4, 3413−3421. (b)
Knirel, Y. A.; Shevelev, S. D.; Perepelov, A. V. Mendeelev Commun.
011, 21, 173−182.
(
7
(
(
1
(
2
(7) (a) Morrison, M. J.; Imperiali, B. Biochemistry 2014, 53, 624−638.
(b) Lewis, A. L.; Desa, N.; Hansen, E. E.; Knirel, Y. A.; Gordon, J. I.;
Gagneux, P.; Nizet, V.; Varki, A. Proc. Natl. Acad. Sci. U.S.A. 2009,
1
06, 13552−13557.
(
8) Boucher, H. W.; Talbot, G. H.; Bradley, J. S.; Edwards, J. E.;
(37) Kumar, A.; Kumar, V.; Dere, R. T.; Schmidt, R. R. Org. Lett.
2011, 13, 3612−3615.
(38) Gouliaras, C.; Lee, D.; Chan, L.; Taylor, M. S. J. Am. Chem. Soc.
Gilbert, D.; Rice, L. B.; Scheld, M.; Spellberg, B.; Bartlett, J. Clin.
Infect. Dis. 2009, 48, 1−12.
(9) Ramphal, R.; Sadoff, J. C.; Pyle, M.; Silipigni, J. D. Infect. Immun.
1984, 44, 38−40.
2011, 133, 13926−13929.
(39) Myhre, D. V.; Smith, F. J. Org. Chem. 1961, 26, 4609−4612.
(40) (a) Martichonok, V.; Whitesides, G. M. J. Org. Chem. 1996, 61,
1702ꢀ1706. (b). Huang, X.; Huang, L.; Wang, H.; Ye, X.ꢀS. Angew.
Chem. Int. Ed. 2004, 43, 5221−5224. (c) Sun, B.; Jiang, H. Tetrahe-
dron Lett. 2011, 52, 6035−6038.
(41) Boons, G. J.; Demchenko, A. V. Chem. Rev. 2000, 100,
4539−4566.
(42) Based on the JH3a/bꢀH4 values (13.6 Hz/4.4 Hz for donor 25 and
3.5 Hz/2.5 Hz for donor 27 respectively), the Pse containing the cyꢀ
clic carbamate moiety adopts a conformation distorted from the chair
form.
(
2
(
2
(
4
10) Castric, P.; Cassels, F. J.; Carlson, R. W. J. Biol. Chem. 2001,
76, 26479−26485.
11) Power, P. M.; Jennings, M. P. FEMS Microbiol. Lett. 2003, 218,
11−222.
12) Dube, D. H.; Champasa, K.; Wang, B. Chem. Commun. 2011,
7, 87−101.
(13) Emmadi, M.; Kulkarni, S. S. Nat. Protocols 2013, 8, 1870−1889.
(14) Knirel, Y. A. Crit. Rev. Microbiol. 1990, 17, 273−304.
(
15) Comer, J. E.; Marshall, M. A.; Blanch, V. J.; Deal, C. D.; Casꢀ
tric, P. Infect. Immun. 2002, 70, 2837−2845.
(
43) Tanase, M.; Imamura, A.; Ando, H.; Ishida, H.; Kiso, M. A Org.
(
(
(
16) Castric, P. Microbiology 1995, 141, 1247−1254.
17) Proft, T.; Baker, E. N. Cell. Mol. Life Sci. 2009, 66, 613−635.
18) Craig, L.; Pique, M. E.; Tainer, J. A. Nat. Rev. Microbiol. 2004,
Lett. 2016, 18, 1454−1457.
(44) Ganesh, N. V.; Sadowska, J. M.; Sarkar, S.; Howells, L.; McGivꢀ
en, J.; Bundle, D. R. J. Am. Chem. Soc. 2014, 136, 16260−16269.
2
, 363−378.
(
45) Clark, E. L.; Emmadi, M.; Krupp, K. L.; Podilapu, A. R.; Helble,
J. D.; Kulkarni, S. S.; Dube, D. H. ACS Chem. Biol. 2016, 11,
365−3373.
46) (a) Bernardes, G. J. L.; Gamblin, D. P.; Davis, B. G. Angew.
(19) Smedley III, J. G.; Jewell, E.; Roguskie, J.; Horzempa, J.;
Syboldt, A.; Stolz, D. B.; Castric, P. Infect. Immun. 2005, 73,
3
(
7
922−7931.
20) Horzempa, J.; Held, T. K.; Cross, A. S.; Furst, D.; Qutyan, M.;
Neely, A. N.; Castric, P. Clin. Vaccine Immunol. 2008, 15, 590−597.
21) Tsvetkov, Y. E.; Shashkov, A. S.; Knirel, Y. A.; Zahringer, U.
(
Chem. Int. Ed. 2006, 45, 4007−4011. (b) Alexander, S. R.; Fairbanks,
A. J. Org. Biomol. Chem. 2016, 14, 6679−6682. (c) Köhling, S.;
Exner, M. P.; Nojoumi, S.; Schiller, J.; Budisa, N.; Rademann, J.
Angew. Chem. Int. Ed. 2016, 53, 15510−15514. (d) Alexander, S. R.;
Lim, D.; Amso, Z.; Brimble, M. A.; Fairbanks, A. J. Org. Biomol.
Chem. 2017, 15, 2152−2156.
(
Carbohydr. Res. 2001, 335, 221−243.
(22) Lee, Y. J.; Kubota, A.; Ishiwata, A.; Ito, Y. Tetrahedron Lett.
2011, 52, 418−421.
(
23) (a) Williams, J. T.; Corcilius, L.; Kiefel, M. J.; Payne, R. J. J.
(
47) Lim, D.; Brimble, M. A.; Kowalczyk, R.; Watson, A. J. A.; Fairꢀ
banks, A. J. Angew. Chem. Int. Ed. 2014, 53, 11907−11911.
48) Munneke, S.; Prevost, J. R. C.; Painter, G. F.; Stocker, B. L.;
Timmer, M. S. M. Org. Lett. 2015, 17, 624−627.
Org. Chem. 2016, 81, 2607−2611. (b) Zunk, M.; Williams, J.; Carter,
J.; Kiefel, M. J. Org. Biomol. Chem. 2014, 12, 2918−2925.
(
(
24) (a) Dhakal, B.; Buda, S.; Crich, D. J. Org. Chem. 2016, 81,
1
2
0617−10630. (b) Popik, O.; Dhakal, B.; Crich, D. J. Org. Chem.
017, 82, 6142−6152.
(25) Matthies, S.; Stallforth, P.; Seeberger, P. H. J. Am. Chem. Soc.
2015, 137, 2848−2851.
(
26) Rotstein, B. H., Winternheimer, D. J.; Yin, L. M.; Deber, C. M.;
Yudin, A. K. Chem. Commun. 2012, 48, 3775−3777.
27) The Barbier reaction was used in the de novo synthesis of KDO
(
and Neu5Ac. For examples, see: (a) Chan, T. H.; Li, C. J. J. Chem.
Soc., Chem. Commun. 1992, 747−748. (b) Gordon, D. M.; Whiteꢀ
ACS Paragon Plus Environment