Contributing to the Study of Enzymatic and Chemical Glycosyl Transfer Through the Observation and Mimicry of Glycosyl Cations

Yves Blériot

doi:10.1055/s-0040-1706073

Synthesis, Table of Contents

Synthesis 2021; 53(05): 904-924
DOI: 10.1055/s-0040-1706073

feature

Contributing to the Study of Enzymatic and Chemical Glycosyl Transfer Through the Observation and Mimicry of Glycosyl Cations

Yves Blériot∗

Abstract

All articles of this category

Abstract

This account describes our efforts dedicated to: 1) the design of glycomimetics aimed at targeting therapeutically relevant carbohydrate processing enzymes, and 2) the observation, characterization, and exploitation of glycosyl cations as a tool for studying the glycosylation reaction. These findings have brought important data regarding this key ionic species as well as innovative strategies to access iminosugars of interest.

1 Introduction

2 The Glycosyl Cation, A Central Species in Glycosciences

2.1 A Selection of the Strategies Developed so far to Gain Insights into Glycosyl Cations Structure

2.2 When Superacids Meet Carbohydrates

3 Chemical Probes to Gain Insights into the Pseudorotational Itinerary of Glycosides During Glycosidic Bond Hydrolysis

3.1 Conformationally Locked Glycosides

3.1.1 The Xylopyranose Case

3.1.2 The Mannopyranose Case

3.2 Conformationally Flexible Iminosugars

3.2.1 Nojirimycin Ring Homologues

3.2.2 Noeuromycin Ring Homologues

3.2.3 Seven-Membered Iminosugar C-Glycosides

4 N-Acetyl-d-glucosamine Mimics

5 Ring Contraction: A Useful Tool to Increase Iminosugar’s Structural Diversity

6 Regioselective Deprotection of Iminosugar C-Glycosides to Introduce Diversity at C2 Position

7 Conclusion

Key words

carbohydrates - glycosyl cation - iminosugars - glycosidases - conformation - superacids

Full Text

References

References

1a Zechel DL, Withers SG. Acc. Chem. Res. 2000; 33: 11
1b Davies G, Sinnott ML, Withers SG. In Comprehensive Biological Catalysis, Vol. 1. Sinnott ML. Academic Press; London: 1997: 119

2 Lillelund VH, Jensen HH, Liang X, Bols M. Chem. Rev. 2002; 102: 515
3 Asano N. Glycobiology 2003; 13: 93R

4a Horenstein NA. Adv. Phys. Org. Chem. 2006; 41: 275
4b Sinnott ML. Carbohydrate Chemistry and Biochemistry . RSC Publishing; Cambridge: 2007
4c Green LG, Ley SV. In Carbohydrates in Chemistry and Biology, Vol. 1. Ernst B, Hart GW, Sinaÿ P. Wiley-VCH; Weinheim: 2000: 427

5a Crich D. Acc. Chem. Res. 2010; 43: 1144
5b Adero PO, Amarasekara H, Wen P, Bohé L, Crich D. Chem. Rev. 2018; 118: 8242

6a van der Vorm S, Hansen T, Overkleeft HS, van der Marel GA, Codée JD. C. Chem. Sci. 2017; 8: 1867
6b Moumé-Pymbock M, Crich D. J. Org. Chem. 2012; 77: 8905
6c Codée JD. C, Walvoort MT. C, de Jong A.-R, Lodder G, Overkleeft HS, van der Marel GA. J. Carbohydr. Chem. 2011; 30: 438
6d Beaver MG, Woerpel KA. J. Org. Chem. 2010; 75: 1107
6e Walvoort MT. C, Dinkelaar J, van den Bos LJ, Lodder G, Overkleeft HS, Codée JD. C, van der Marel GA. Carbohydr. Res. 2010; 345: 1252
6f Lucero CG, Woerpel KA. J. Org. Chem. 2006; 71: 2641
6g Crich D, Vinogradova O. J. Org. Chem. 2006; 71: 8473
6h Krumper JR, Salamant WA, Woerpel KA. Org. Lett. 2008; 10: 4907
6i Zhu X, Kawatkar S, Rao Y, Boons G.-J. J. Am. Chem. Soc. 2006; 128: 11948
6j Ishiwata A, Akao H, Ito Y. Org. Lett. 2006; 8: 5525
6k Larsen CH, Ridgway BH, Shaw JT, Smith DM, Woerpel KA. J. Am. Chem. Soc. 2005; 127: 10879
6l Ayala L, Lucero CG, Romero JA. C, Tabacco SA, Woerpel KA. J. Am. Chem. Soc. 2003; 125: 15521
6m Romero JA. C, Tabacco SA, Woerpel KA. J. Am. Chem. Soc. 2000; 122: 168
6n Parent J.-F, Deslongchamps P. Org. Biomol. Chem. 2016; 14: 11183

7a Unligil UM, Rini JM. Curr. Opin. Struct. Biol. 2000; 10: 510
7b Rye CS, Withers SG. Curr. Opin. Chem. Biol. 2000; 4: 573
7c See ref. 1a.

8 von Itzstein M, Wu W-Y, Kok GB, Pegg MS, Dyason JC, Jin B, Phan TV, Smythe ML, White HF, Oliver SW, Colman PM, Varghese JN, Ryan DM, Woods JM, Bethell RC, Hotham VJ, Cameron JM, Penn CR. Nature 1993; 363: 418
9 Scott LJ, Spencer CM. Drugs 2000; 59: 521
10 Goss PE, Baker MA, Carver JP, Dennis JW. Clin. Cancer Res. 1995; 1: 935
11 Gloster TM, Meloncelli P, Stick RV, Zechel D, Vasella A, Davies GJ. J. Am. Chem. Soc. 2007; 129: 2345

12a Svansson L, Johnston BD, Gu JH, Patrick B, Pinto BM. J. Am. Chem. Soc. 2000; 122: 10769
12b Heck M.-P, Vincent SP, Murray BW, Bellamy F, Wong C.-H, Mioskowski C. J. Am. Chem. Soc. 2004; 126: 1971
12c Davis BG, Hull A, Smith C, Nash RJ, Watson AA, Winkler DA, Griffiths RC, Fleet GW. J. Tetrahedron: Asymmetry 1998; 9: 2947
12d Tong MK, Papandreou G, Ganem B. J. Am. Chem. Soc. 1990; 112: 6137
12e Williams SJ, Notenboom V, Wicki J, Rose DR, Withers SG. J. Am. Chem. Soc. 2000; 122: 4229

13 Davies GJ, Ducros VM.-A, Varrot A, Zechel DL. Biochem. Soc. Trans. 2003; 31: 523
14 Sasaki K, Isoda R. Trends Glycosc. Glycotechnol. 2020; 32: E87
15 Frihed TG, Bols M, Pedersen CM. Chem. Rev. 2015; 115: 4963
16 Hosoya T, Takano T, Kosma P, Rosenau T. J. Org. Chem. 2014; 79: 7889
17 Suga S, Suzuki S, Yamamoto A, Yoshida J.-I. J. Am. Chem. Soc. 2000; 122: 10244
18 Suzuki S, Matsumoto K, Kawamura K, Suga S, Yoshida J.-I. Org. Lett. 2004; 6: 3755

19a Matsumoto K, Ueoka K, Suzuki S, Suga S, Yoshida J.-I. Tetrahedron 2009; 65: 10901
19b Saito K, Ueoka K, Matsumoto K, Suga S, Nokami T, Yoshida J.-I. Angew. Chem. Int. Ed. 2011; 50: 5153

20a Yang MT, Woerpel KA. J. Org. Chem. 2009; 74: 545
20b Chamberland S, Ziller JW, Woerpel KA. J. Am. Chem. Soc. 2005; 127: 5322

21 See refs. 6h, 6l, 6m.

22a Nukada T, Bérces A, Wang L, Zgierski MZ, Whitfield DM. Carbohydr. Res. 2005; 340: 841
22b Ionescu AR, Whitfield DM, Zgierski MZ, Nukada T. Carbohydr. Res. 2006; 341: 2912
22c Whitfield DM. Carbohydr. Res. 2012; 356: 180
22d Whitfield DM. Carbohydr. Res. 2012; 356: 191

23a Denekamp C, Sandlers Y. J. Mass Spectrom. 2005; 40: 765
23b Denekamp C, Sandlers Y. J. Mass Spectrom. 2005; 40: 1055

24 Elferink H, Severijnen ME, Martens J, Mensink RA, Berden G, Oomens J, Rutjes FP. J. T, Rijs AM, Boltje TJ. J. Am. Chem. Soc. 2018; 140: 6034
25 Mucha E, Marianski M, Xu F.-F, Thomas DA, Meijer G, von Helden G, Seeberger PH, Pagel K. Nat. Commun. 2018; 9: 4174
26 Marianski M, Mucha E, Greis K, Moon S, Pardo A, Kirschbaum C, Thomas DA, Meijer G, von Helden G, Gilmore K, Seeberger PH, Pagel K. Angew. Chem. Int. Ed. 2020; 59: 6166
27 Huang M, Garrett GE, Birlirakis N, Bohé L, Pratt DA, Crich D. Nat. Chem. 2012; 4: 663
28 National Research Council, Transforming Glycoscience: A Roadmap for the Future. The National Academies Press; Washington DC: 2012
29 Amyes TL, Jencks WP. J. Am. Chem. Soc. 1989; 111: 7888
30 Winstein S, Clippinger E, Fainberg AH, Heck R, Robinson GC. J. Am. Chem. Soc. 1956; 78: 328
31 Olah GA, Laali KK, Wang Q, Prakash GK. S. Onium Ions . Wiley; New York: 1998
32 Hall NF, Conant JB. J. Am. Chem. Soc. 1927; 49: 3047
33 Olah GA. Angew. Chem. Int. Ed. 1973; 12: 173
34 Gillespie RJ, Peel TE. J. Am. Chem. Soc. 1973; 95: 5173
35 Olah GA, Prakash GK. S, Molnar A, Sommer J. Superacid Chemistry . Wiley; Hoboken: 2009
36 Gillespie RJ, Liang J. J. Am. Chem. Soc. 1988; 110: 6053
37 Martin A, Arda A, Désiré J, Martin-Mingot A, Probst N, Sinaÿ P, Jiménez-Barbero J, Thibaudeau S, Blériot Y. Nat. Chem. 2016; 8: 186
38 Bennett CS, Galan MC. Chem. Rev. 2018; 118: 7931
39 Namchuk MN, McCarter JD, Becalski A, Andrews T, Withers SG. J. Am. Chem. Soc. 2000; 122: 1270
40 Riddlestone IM, Kraft A, Schaefer J, Krossing I. Angew. Chem. Int. Ed. 2018; 57: 13982
41 Hansen T, Lebedel L, Remmerswaal WA, van der Vorm S, Wander DP. A, Overkleeft HS, Filippov DV, Désiré J, Martin-Mingot A, Blériot Y, van der Marel GA, Thibaudeau S, Codée JD. C. ACS Cent. Sci. 2019; 5: 781
42 Bennet AJ, Kitos TE. J. Chem. Soc., Perkin Trans. 2 2002; 1207
43 See ref. 1b.
44 See ref. 13.
45 Vasella A, Davies G, Böhm M. Curr. Opin. Chem. Biol. 2002; 6: 619

46a Bennet AJ, Sinnott ML. J. Am. Chem. Soc. 1986; 108: 7287
46b Huang X, Tanaka KS. E, Bennet AJ. J. Am. Chem. Soc. 1997; 119: 11147

47a Whitfield DM. Adv. Carbohydr. Chem. Biochem. 2009; 62: 83
47b Kim J.-H, Yang H, Khot V, Whitfield D, Boons G.-J. Eur. J. Org. Chem. 2006; 5007

48 Vocadlo DJ, Davies GJ. Curr. Opin. Chem. Biol. 2008; 12: 539
49 Nerinckx W, Desmet T, Claeyssens M. ARKIVOC 2006; (xiii): 90
50 Sabini E, Sulzenbacher G, Dauter M, Dauter Z, Jorgensen PL, Schülein M, Dupont C, Davies GJ, Wilson KS. Chem. Biol. 1999; 6: 483
51 Blériot Y, Vadivel SK, Greig IR, Kirby AJ, Sinaÿ P. Tetrahedron Lett. 2003; 44: 6687

52a Das SK, Mallet J.-M, Esnault J, Driguez P.-A, Duchaussoy P, Sizun P, Hérault J.-P, Herbert J.-M, Petitou M, Sinaÿ P. Angew. Chem. Int. Ed. 2001; 40, 1670
52b Das SK, Mallet J.-M, Esnault J, Driguez P.-A, Duchaussoy P, Sizun P, Hérault J.-P, Herbert J.-M, Petitou M, Sinaÿ P. Chem. Eur. J. 2001; 7: 4821

53 Herrera AJ, Beneitez MT, Amorim L, Javier Cañada F, Jiménez-Barbero J, Sinaÿ P, Blériot Y. Carbohydr. Res. 2007; 342: 1876
54 Wang C.-C, Kulkarni SS, Lee J.-C, Luo S.-Y, Hung S.-C. Nat. Protoc. 2008; 3: 97
55 Amorim L, Marcelo F, Rousseau C, Nieto L, Jiménez-Barbero J, Marrot J, Rauter AP, Sollogoub M, Bols M, Blériot Y. Chem. Eur. J. 2011; 17: 7345

56a Crich D, Li L. J. Org. Chem. 2007; 72: 1681
56b Crich D, Chandrasekera NS. Angew. Chem. Int. Ed. 2004; 43: 5386

57 Ducros VM.-A, Zechel DL, Murshudov GN, Gilbert HJ, Szabo L, Stoll D, Withers SG, Davies GJ. Angew. Chem. Int. Ed. 2002; 41: 2824
58 Stoddart JF. Stereochemistry of Carbohydrates . Wiley Interscience; Toronto: 1971
59 Amorim L, Díaz D, Calle-Jiménez LP, Jiménez-Barbero J, Sinaÿ P, Blériot Y. Tetrahedron Lett. 2006; 47: 8887
60 Compain P, Martin OR. Iminosugars: From Synthesis to Therapeutic Applications. Wiley-VCH; Weinheim: 2007
61 Horne G, Wilson FX. Prog. Med. Chem. 2011; 50: 135
62 Paulsen H, Todt K. Chem. Ber. 1967; 100: 512

For tetrahydroxyazepanes, see:

63a Dax K, Gaigg B, Grassberger V, Kölblinger B, Stütz AE. J. Carbohydr. Chem. 1990; 9: 479
63b Farr RA, Holland AK, Huber EW, Peet NP, Weintraub PM. Tetrahedron 1994; 50: 1033
63c Lohray BB, Jayamma Y, Chatterjee M. J. Org. Chem. 1995; 60: 5958
63d Lohray BB, Bhushan V, Prasuna G, Jayamma Y, Raheem MA, Papireddy P, Umadevi B, Premkumar M, Lakshmi NS, Narayanareddy K. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1999; 38: 1311
63e Qian X, Moris-Varas F, Wong C.-H. Bioorg. Med. Chem. Lett. 1996; 6: 1117
63f Moris-Varas F, Qian X.-H, Wong C.-H. J. Am. Chem. Soc. 1996; 118: 7647
63g Qian X, Moris-Varas F, Fitzgerald MC, Wong C.-H. Bioorg. Med. Chem. 1996; 4: 2055
63h Le Merrer Y, Poitout L, Depezay J.-C, Dosbaa I, Geoffroy S, Foglietti M.-J. Bioorg. Med. Chem. 1997; 5: 519
63i Johnson HA, Thomas NR. Bioorg. Med. Chem. Lett. 2002; 12: 237
63j Andreana PR, Sanders T, Janczuk A, Warrick JI, Wang PG. Tetrahedron Lett. 2002; 43: 6525
63k Joseph CC, Regeling H, Zwanenburg B, Chittenden GJ. F. Tetrahedron 2002; 58: 6907
63l Fuentes J, Gasch C, Olano D, Pradera MA, Repetto G, Sayago FJ. Tetrahedron: Asymmetry 2002; 13: 1743
63m Painter GF, Eldridge PG, Falshaw A. Bioorg. Med. Chem. 2004; 12: 225

For trihydroxyazepanes, see:

63n Andersen SM, Ekhart C, Lundt I, Stütz AE. Carbohydr. Res. 2000; 326: 22
63o Gallos JK, Demeroudi SC, Stathopoulou CC, Dellios CC. Tetrahedron Lett. 2001; 42: 7497
63p Dhavale DD, Chaudhari VD, Tilekar JN. Tetrahedron Lett. 2003; 44: 7321

64 Inouye S, Tsuruoka T, Niida T. J. Antibiot. (Tokyo) 1966; 19: 288
65 Sellier O, Van de Weghe P, Le Nouen D, Strehler C, Eustache J. Tetrahedron Lett. 1999; 40: 853

66a Li H, Blériot Y, Chantereau C, Mallet J.-M, Sollogoub M, Zhang Y, Rodriguez-Garcia E, Vogel P, Jiménez-Barbero J, Sinaÿ P. Org. Biomol. Chem. 2004; 2: 1492
66b Li H, Blériot Y, Mallet J.-M, Zhang Y, Rodriguez-Garcia E, Vogel P, Mari S, Jiménez-Barbero J, Sinaÿ P. Heterocycles 2004; 64: 65

67a Li H, Blériot Y, Mallet J.-M, Rodriguez-Garcia E, Vogel P, Zhang Y, Sinaÿ P. Tetrahedron: Asymmetry 2005; 16: 313
67b Li H, Schütz C, Favre S, Zhang Y, Vogel P, Sinaÿ P, Blériot Y. Org. Biomol. Chem. 2006; 4: 1653

68a Martinez-Mayorga K, Medina-Franco JL, Mari S, Cañada FJ, Rodriguez-Garcia E, Vogel P, Li H, Blériot Y, Sinaÿ P, Jiménez-Barbero J. Eur. J. Org. Chem. 2004; 4119
68b Pérez-Castells J, Fontanella M, Arda A, Cañada FJ, Sollogoub M, Blériot Y, Jiménez-Barbero J. New J. Chem. 2012; 36: 1008

69a Dhavale DD, Markad SD, Karanjule NS, PrakashaReddy J. J. Org. Chem. 2004; 69: 4760
69b Pino-González MS, Assiego C, López-Herrera FJ. Tetrahedron Lett. 2003; 44: 8353
69c Assiego C, Pino-González MS, López-Herrera FJ. Tetrahedron Lett. 2004; 45: 2611
69d Saavedra OM. Ph.D. Dissertation . Orleans University; France: 1998

70 Liu H, Liang X, Sohoel H, Bülow A, Bols M. J. Am. Chem. Soc. 2001; 123: 5116
71 Liu H, Lillelund VH, Andersch J, Liang X, Bols M. J. Carbohydr. Chem. 2004; 23: 223
72 Liptak A, Jodal I, Nanasi P. Carbohydr. Res. 1975; 44: 1
73 Bräse S, Gil C, Knepper K, Zimmermann V. Angew. Chem. Int. Ed. 2005; 44: 5188
74 Deschamp J, Mondon M, Nakagawa S, Kato A, Alonzi DS, Butters TD, Zhang Y, Sollogoub M, Blériot Y. Bioorg. Med. Chem. 2012; 20: 641
75 Butters TD, Alonzi DS, Kukushkin NV, Ren Y, Blériot Y. Glycoconjugate J. 2009; 26: 1109
76 Li H, Zhang Y, Vogel P, Sinaÿ P, Blériot Y. Chem. Commun. 2007; 183
77 Li H, Liu T, Zhang Y, Favre S, Bello C, Vogel P, Butters TD, Oikonomakos NG, Marrot J, Blériot Y. ChemBioChem 2008; 9: 253
78 Compain P. In Iminosugars: From Synthesis to Therapeutic Applications . Compain P, Martin OR. Wiley-VCH; Weinheim: 2007: 63

79a Wennekes T, van den Berg RJ. B. H. N, Boltje TJ, Donker-Koopman WE, Kuijper B, van der Marel GA, Strijland A, Verhagen CP, Aerts JM. F. G, Overkleeft HS. Eur. J. Org. Chem. 2010; 1258
79b Schönemann W, Galienne E, Compain P, Ikeda K, Asano N, Martin OR. Bioorg. Med. Chem. 2010; 18: 2645

80 Compain P, Chagnault V, Martin OR. Tetrahedron: Asymmetry 2009; 20: 672

81a Otero JM, Estévez AM, Soengas RG, Estévez JC, Nash RJ, Fleet GW. J, Estévez RJ. Tetrahedron: Asymmetry 2008; 19: 2443
81b Tite T, Tsimilaza A, Lallemand M.-C, Tillequin F, Leproux P, Libot F, Husson H.-P. Eur. J. Org. Chem. 2006; 863

82 Désiré J, Mondon M, Fontelle N, Nakagawa S, Hirokami Y, Adachi I, Iwaki R, Fleet GW. J, Alonzi DS, Twigg G, Butters TD, Bertrand J, Cendret V, Becq F, Norez C, Marrot J, Kato A, Blériot Y. Org. Biomol. Chem. 2014; 12: 8977
83 Fontelle N, Yamamoto A, Arda A, Jiménez-Barbero J, Kato A, Désiré J, Blériot Y. Eur. J. Org. Chem. 2018; 5477
84 Bartolo ND, Read JA, Valentín EM, Woerpel KA. Chem. Rev. 2020; 120: 1513
85 Granier T, Vasella A. Helv. Chim. Acta 1998; 81: 865
86 Shitara E, Nishimura Y, Kojima F, Takeuchi T. Bioorg. Med. Chem. 1999; 7: 1241
87 Kondo K.-I, Adachi H, Shitara E, Kojima F, Nishimura Y. Bioorg. Med. Chem. 2001; 9: 1091
88 van den Berg RJ. B. H. N, Donker-Koopman W, van Boom JH, Aerts HM. F. G, Noort D. Bioorg. Med. Chem. 2004; 12: 891
89 Cantarel BL, Coutinho PM, Rancurel C, Bernard T, Lombard V, Henrissat B. Nucleic Acids Res. 2009; 37: D233
90 Stubbs KA, Balcewich M, Mark BL, Vocadlo DJ. J. Biol. Chem. 2007; 282: 21382
91 Liu T, Chen L, Ma Q, Shen X, Yang Q. Curr. Pharm. Des. 2014; 20: 754
92 Liu T, Duan Y, Yang Q. Biotechnol. Adv. 2018; 36: 1127
93 Butkinaree C, Park K, Hart GW. Biochim. Biophys. Acta 2010; 1800: 96
94 Cheng Q, Li H, Merdek K, Park JT. J. Bacteriol. 2000; 182: 4836
95 Asgarali A, Stubbs KA, Oliver A, Vocadlo DJ, Mark BL. Antimicrob. Agents Chemother. 2009; 53: 2274
96 Stubbs KA, Bacik J.-P, Perley-Robertson GE, Whitworth GE, Gloster TM, Vocadlo DJ, Mark BL. ChemBioChem 2013; 14: 1973
97 Yamaguchi T, Blazquez B, Hesek D, Lee M, Llarrull LI, Boggess B, Oliver AG, Fisher JF, Mobashery S. ACS Med. Chem. Lett. 2012; 3: 238
98 Merzendorfer H, Zimoch L. J. Exp. Biol. 2003; 206: 4393
99 Mahuran DJ. Biochim. Biophys. Acta 1999; 1455: 105
100 Platt FM. Nature 2014; 510: 68
101 Gao Y, Wells L, Comer FI, Parker GJ, Hart GW. J. Biol. Chem. 2001; 276: 9838
102 Torres CR, Hart GW. J. Biol. Chem. 1984; 259: 3308
103 Hart GW, Housley MP, Slawson C. Nature 2007; 446: 1017

104a Singh JP, Zhang K, Wu J, Yang X. Cancer Lett. 2015; 356: 244
104b Issad T, Masson E, Pagesy P. Diabetes Metab. 2010; 36: 423
104c Frenkel-Pinter M, Shmueli MD, Raz C, Yanku M, Zilberzwige S, Gazit E, Segal D. Sci. Adv. 2017; 3: e1601576

105 Vocadlo DJ, Withers SG. Biochemistry 2005; 44: 12809
106 Balcewich MD, Stubbs KA, He Y, James TW, Davies GJ, Vocadlo DJ, Mark BL. Protein Sci. 2009; 18: 1541
107 Bouzard D, Di Cesare P, Essiz M, Jacquet JP, Kiechel JR, Remuzon P, Weber A, Oki T, Masuyoshi M, Kessler RE, Fung-Tomc J, Desiderio J. J. Med. Chem. 1990; 33: 1344
108 Mondon M, Hur S, Vadlamani G, Rodrigues P, Tsibina P, Oliver A, Mark BL, Vocadlo DJ, Blériot Y. Chem. Commun. 2013; 49: 10983
109 Bouquet J, King DT, Vadlamani G, Benzie GR, Iorga B, Ide D, Adachi I, Kato A, Vocadlo DJ, Mark BL, Blériot Y, Désiré J. Org. Biomol. Chem. 2017; 15: 4609
110 Rao FV, Dorfmueller HC, Villa F, Allwood M, Eggleston IM, van Aalten DM. F. EMBO J. 2006; 25: 1569
111 Yuzwa SA, Macauley MS, Heinonen JE, Shan X, Dennis RJ, He Y, Whitworth GE, Stubbs KA, McEachern EJ, Davies GJ, Vocadlo DJ. Nat. Chem. Biol. 2008; 4: 483
112 Beer D, Maloisel J.-L, Rast DM, Vasella A. Helv. Chim. Acta 1990; 73: 1918
113 Poitout L, Le Merrer Y, Depezay J.-C. Tetrahedron Lett. 1994; 35: 3293
114 Clarke JT. R, Mahuran DJ, Sathe S, Kolodny EH, Rigat BA, Raiman JA, Tropak MB. Mol. Genet. Metab. 2011; 102: 6
115 Patzel KA, Yardeni T, Le Poëc-Celic E, Leoyklang P, Dorward H, Alonzi DS, Kukushkin NV, Xu B, Zhang Y, Sollogoub M, Blériot Y, Gahl WA, Huizing M, Butters TD. J. Inherited Metab. Dis. 2014; 37: 297
116 Hinderlich S, Stäsche R, Zeitler R, Reutter W. J. Biol. Chem. 1997; 272: 24313
117 Eisenberg I, Avidan N, Potikha T, Hochner H, Chen M, Olender T, Barash M, Shemesh M, Sadeh M, Grabov-Nardini G, Shmilevich I, Friedmann A, Karpati G, Bradley WG, Baumbach L, Lancet D, Ben Asher E, Beckmann JS, Argov Z, Mitrani-Rosenbaum S. Nat. Genet. 2001; 29: 83
118 Compain P. Chem. Rec. 2020; 20: 1

119a Cecioni S, Imberty A, Vidal S. Chem. Rev. 2015; 115: 525
119b Deniaud D, Julienne K, Gouin SG. Org. Biomol. Chem. 2011; 9: 966

120a Kitov PI, Sadowska JM, Mulvey G, Armstrong GD, Ling H, Pannu NS, Read RJ, Bundle DR. Nature 2000; 403: 669
120b Pertici F, Pieters RJ. Chem. Commun. 2012; 48: 4008

121 Alvarez-Dorta D, King DT, Legigan T, Ide D, Idachi I, Deniaud D, Désiré J, Kato A, Vocadlo D, Gouin S, Blériot Y. Chem. Eur. J. 2017; 23: 9022

122a Poitout L, Le Merrer Y, Depezay J.-C. Tetrahedron Lett. 1996; 37: 1613
122b Bagal SK, Davies SG, Lee JA, Roberts PM, Russell AJ, Scott PM, Thomson JE. Org. Lett. 2010; 12: 136

123 Lohray BB, Prasuna G, Jayamma Y, Raheem MA. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1997; 36: 220

124a D’Alonzo D, Guaragna A, Palumbo G. Curr. Med. Chem. 2009; 16: 473
124b Jenkinson SF, Fleet GW. J, Nash RJ, Koike Y, Adachi I, Yoshihara A, Morimoto K, Izumori K, Kato A. Org. Lett. 2011; 13: 4064

125 Métro T.-X, Duthion B, Gomez Pardo D, Cossy J. Chem. Soc. Rev. 2010; 39: 89
126 Fontelle N. Ph.D. Dissertation . Université de Poitiers; France: 2013
127 Liu S.-W, Chen C.-S, Chang S.-S, Mong K.-KT, Lin C.-H, Chang C.-W, Tang CY, Li Y.-K. Biochemistry 2009; 48: 110
128 Liu T.-W, Ho C.-W, Huang H.-H, Chang S.-M, Popat SD, Wang Y.-T, Wu M.-S, Chen Y.-J, Lin C.-H. Proc. Natl. Acad. Sci. U.S.A. 2009; 106: 14581
129 Willems PJ, Seo H.-C, Coucke P, Tonlorenzi R, O’Brien JS. Eur. J. Hum. Genet. 1999; 7: 60
130 Liu T, Zhang Y, Blériot Y. Synlett 2007; 905
131 Lammerts van Bueren A, Fayers-Kerr J, Luo B, Zhang Y, Sollogoub M, Blériot Y, Rovira C, Davies GJ. J. Am. Chem. Soc. 2010; 132: 1804

132a Blériot Y, Tran AT, Prencipe G, Jagadeesh Y, Auberger N, Zhu S, Gauthier C, Zhang Y, Désiré J, Adachi I, Kato A, Sollogoub M. Org. Lett. 2014; 16: 5516
132b Blériot Y, Auberger N, Jagadeesh Y, Gauthier C, Prencipe G, Tran AT, Marrot J, Désiré J, Yamamoto A, Sollogoub M. Org. Lett. 2014; 16: 5512

For another example of 2-acetamidohomoiminosugar, see:

132c Hsu C.-H, Schelwies M, Enck S, Huang L.-Y, Huang S.-H, Chang Y.-F, Cheng T.-JR, Cheng W.-C, Wong C.-H. J. Org. Chem. 2014; 79: 8629

133a Kite GC, Horn JM, Romeo JT, Fellows LE, Leest DC, Scofield AM, Smith NG. Phytochemistry 1990; 29: 103
133b Kite GC, Fellows LE, Fleet GW. J, Liu PS, Scofield AM, Smith NG. Tetrahedron Lett. 1988; 29: 6483

For β-HNJ, see:

133c Asano N, Kato A, Miyauchi M, Kizu H, Kameda Y, Watson AA, Nash RJ, Fleet GW. J. J. Nat. Prod. 1998; 61: 625
133d Asano N, Nishida M, Kizu H, Matsui K, Watson AA, Nash RJ. J. Nat. Prod. 1997; 60: 98

134a Liu PS. J. Org. Chem. 1987; 52: 4717
134b Martin OR, Liu L, Yang F. Tetrahedron Lett. 1996; 37: 1991
134c Martin OR, Saavedra OM. Tetrahedron Lett. 1995; 36: 799

135 Dhavale DD, Matin MM. ARKIVOC 2005; (iii): 110

136a Megia-Fernandez A, Morales-Sanfrutos J, Hernandez-Mateo F, Santoyo-Gonzalez F. Curr. Org. Chem. 2011; 15: 401
136b Byun H.-S, He L, Bittman R. Tetrahedron 2000; 56: 7051

137 Jagadeesh Y, Tran AT, Luo B, Auberger N, Désiré J, Nakagawa S, Kato A, Zhang Y, Sollogoub M, Blériot Y. Org. Biomol. Chem. 2015; 13: 3446

138a Dondoni A, Giovannini PP, Perrone D. J. Org. Chem. 2005; 70: 5508
138b Godin G, Compain P, Martin OR. Org. Lett. 2003; 5: 3269

139 Cipolla L, Lay L, Nicotra F. J. Org. Chem. 1997; 62: 6678
140 Rychnovsky SD, Bartlett PA. J. Am. Chem. Soc. 1981; 103: 3963
141 Cipolla L, La Ferla B, Peri F, Nicotra F. Chem. Commun. 2000; 1289
142 Foucart Q, Marrot J, Désiré J, Blériot Y. Org. Lett. 2019; 21: 4821

143a Smith DM, Woerpel KA. Org. Biomol. Chem. 2006; 4: 1195
143b Heuckendorf M, Pedersen CM, Bols M. Chem. Eur. J. 2010; 16: 13982