Organic & Biomolecular Chemistry
Paper
partially based on research done within the framework of 16 R. T. Almaraz, U. Aich, H. S. Khanna, E. Tan,
COST Action CA18103 (INNOGLY) supported by European
Cooperation in Science and Technology. RH and PV were sup-
R. Bhattacharya, S. Shah and K. J. Yarema, Biotechnol.
Bioeng., 2012, 109, 992–1006.
ported by MH CZ - DRO (MMCI, 00209805). MB acknowledges 17 K. Qin, H. Zhang, Z. Zhao and X. Chen, J. Am. Chem. Soc.,
support from Karel Berka (Palacky University Olomouc) for the 2020, 142, 9382–9388.
access to TURBOMOLE, MacroModel, LigPrep, COSMOThermX 18 M. Kurfiřt, L. Červenková Št’astná, M. Dračínský,
and COSMOperm calculations.
M. Müllerová, V. Hamala, P. Cuřínová and J. Karban, J. Org.
Chem., 2019, 84, 6405–6431.
19 V. Hamala, L. Červenková Šťastná, M. Kurfiřt, P. Cuřínová,
M. Dračínský and J. Karban, Org. Biomol. Chem., 2020, 18,
5427–5434.
Notes and references
1 B. Linclau, A. Arda, N. C. Reichardt, M. Sollogoub, 20 L.-X. Wang, N. Sakairi and H. Kuzuhara, J. Chem. Soc.,
L. Unione, S. P. Vincent and J. Jimenez-Barbero, Chem. Soc.
Rev., 2020, 49, 3863–3888.
Perkin Trans. 1, 1990, 1677–1682.
21 Z. A. Morrison and M. Nitz, Carbohydr. Res., 2020, 495, 108071.
2 S. Goon and C. R. Bertozzi, J. Carbohydr. Chem., 2002, 21, 22 M. Sharma, G. G. Potti, O. D. Simmons and W. Korytnyk,
943–977. Carbohydr. Res., 1987, 162, 41–51.
3 C. D. Rillahan, A. Antonopoulos, C. T. Lefort, R. Sonon, 23 M. Kurfiřt, L. Č. Šťastná, P. Cuřínová, V. Hamala and
P. Azadi, K. Ley, A. Dell, S. M. Haslam and J. C. Paulson,
Nat. Chem. Biol., 2012, 8, 661–668.
4 T. Heise, J. F. A. Pijnenborg, C. Büll, N. van Hilten,
J. Karban, J. Org. Chem., 2021, 86, 5073–5090.
24 A. V. Demchenko, M. A. Wolfert, B. Santhanam, J. N. Moore
and G.-J. Boons, J. Am. Chem. Soc., 2003, 125, 6103–6112.
E. D. Kers-Rebel, N. Balneger, H. Elferink, G. J. Adema and 25 P.-C. Lin, A. K. Adak, S.-H. Ueng, L.-D. Huang, K.-T. Huang,
T. J. Boltje, J. Med. Chem., 2019, 62, 1014–1021.
J.-a. A. Ho and C.-C. Lin, J. Org. Chem., 2009, 74, 4041–
5 N. M. Okeley, S. C. Alley, M. E. Anderson, T. E. Boursalian,
4048.
P. J. Burke, K. M. Emmerton, S. C. Jeffrey, K. Klussman, 26 V. Hamala, L. Červenková Št’astná, M. Kurfiřt, P. Cuřínová,
C.-L. Law, D. Sussman, B. E. Toki, L. Westendorf, W. Zeng,
X. Zhang, D. R. Benjamin and P. D. Senter, Proc. Natl. Acad.
Sci. U. S. A., 2013, 110, 5404–5409.
M. Dračínský and J. Karban, Beilstein J. Org. Chem., 2021,
accepted, Beilstein Arch. 2021, 202110. DOI: 10.3762/
bxiv.2021.10.v1.
6 J. G. Allen, M. Mujacic, M. J. Frohn, A. J. Pickrell, 27 C. Mersch, S. Wagner and A. Hoffmann-Röder, Synlett,
P. Kodama, D. Bagal, T. San Miguel, E. A. Sickmier, 2009, 2167–2171.
S. Osgood, A. Swietlow, V. Li, J. B. Jordan, K.-W. Kim, A.-M. 28 R. V. Kolakowski, N. Shangguan, R. R. Sauers and
C. Rousseau, Y.-J. Kim, S. Caille, M. Achmatowicz, O. Thiel, L. J. Williams, J. Am. Chem. Soc., 2006, 128, 5695–5702.
C. H. Fotsch, P. Reddy and J. D. McCarter, ACS Chem. Biol., 29 J. Karban, M. Budesinsky, M. Cerny and T. Trnka, Collect.
2016, 11, 2734–2743. Czech. Chem. Commun., 2001, 66, 799–819.
7 S. R. Barthel, A. Antonopoulos, F. Cedeno-Laurent, 30 D. Hesek, M. Lee, W. Zhang, B. C. Noll and S. Mobashery,
L. Schaffer, G. Hernandez, S. A. Patil, S. J. North, A. Dell, J. Am. Chem. Soc., 2009, 131, 5187–5193.
K. L. Matta, S. Neelamegham, S. M. Haslam and 31 M. Adinolfi, G. Barone, L. Guariniello and A. Iadonisi,
C. J. Dimitroff, J. Biol. Chem., 2011, 286, 21717–21731. Tetrahedron Lett., 1999, 40, 8439–8441.
8 S.-I. Nishimura, M. Hato, S. Hyugaji, F. Feng and 32 Thioaglycon migration did not occur in an appreciable
M. Amano, Angew. Chem., Int. Ed., 2012, 51, 3386–3390. extent in agreement with our findings reported in ref. 26.
9 M. Sharma, R. J. Bernacki, M. J. Hillman and W. Korytnyk, 33 S. M. Andersen, M. Heuckendorff and H. H. Jensen, Org.
Carbohydr. Res., 1993, 240, 85–93. Lett., 2015, 17, 944–947 and references therein.
10 M. Sharma, R. J. Bernacki, B. Paul and W. Korytnyk, 34 T. Yamaguchi, D. Hesek, M. Lee, A. G. Oliver and
Carbohydr. Res., 1990, 198, 205–221. S. Mobashery, J. Org. Chem., 2010, 75, 3515–3517.
11 Y. Dai, R. Hartke, C. Li, Q. Yang, J. O. Liu and L. X. Wang, 35 E. M. Nashed and C. P. J. Glaudemans, J. Org. Chem., 1987,
ACS Chem. Biol., 2020, 15, 2662–2672. 52, 5255–5260.
12 S. Horník, L. Červenková Šťastná, P. Cuřínová, J. Sýkora, 36 S. J. Richards, T. Keenan, J. B. Vendeville, D. E. Wheatley,
K. Káňová, R. Hrstka, I. Císařová, M. Dračínský and
J. Karban, Beilstein J. Org. Chem., 2016, 12, 750–759.
13 U. Aich, C. T. Campbell, N. Elmouelhi, C. A. Weier,
S. G. Sampathkumar, S. S. Choi and K. J. Yarema, ACS
Chem. Biol., 2008, 3, 230–240.
14 Z. Wang, J. Du, P.-L. Che, M. A. Meledeo and K. J. Yarema,
Curr. Opin. Chem. Biol., 2009, 13, 565–572.
15 C. T. Saeui, L. Liu, E. Urias, J. Morrissette-McAlmon,
H. Chidwick, D. Budhadev, C. E. Council, C. S. Webster,
H. Ledru, A. N. Baker, M. Walker, M. C. Galan, B. Linclau,
M. A. Fascione and M. I. Gibson, Chem. Sci., 2021, 12, 905–
910.
37 L. Rochepeau-Jobron and J.-C. Jacquinet, Carbohydr. Res.,
1998, 305, 181–191.
38 K. J. Gregg, M. D. L. Suits, L. Deng, D. J. Vocadlo and
A. B. Boraston, J. Biol. Chem., 2015, 290, 25657–25669.
R. Bhattacharya and K. J. Yarema, Mol. Pharm., 2018, 15, 39 G. Shaw, S. Morse, M. Ararat and F. L. Graham, FASEB J.,
705–720.
2002, 16, 869–871.
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