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Coupling and Decoupling of Diverse Molecular Units in Glycosciences pp 155–166Cite as

Recognition of Thiols in Coupling Reactions to Organic and Carbohydrate Acceptors

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Abstract

Reactions of thiols in thio-click coupling processes with various reactive systems (including carbohydrates) are compiled. A selection of simple and complex thiols in stereoselective and non-stereoselective approaches recognizing their reactivity is also reviewed. Solvents, employed in the discussed processes including water, are briefly discussed as well.

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References

  1. Bielski R, Witczak ZJ (2013) Strategies of coupling molecular units when later decoupling is needed. Chem Rev 113:2205–2243

    Article  CAS  Google Scholar 

  2. Hoyle CE, Bowman CN (2010) Thiol-ene click chemistry. Angew Chem Int Ed 49:1540–1573

    Article  CAS  Google Scholar 

  3. Nair DP, Podgoŕski M, Chatani S, Gong T, Xi W, Fenoli CR, Bowman CN (2014) The thiol-michael addition click reaction: a powerful and widely used tool in materials chemistry. Chem Mater 26:724–744

    Article  CAS  Google Scholar 

  4. Witczak ZJ (2013) Thio-click chemistry in glycosciences: overview and perspectives. In: Witczak ZJ, Bielski R (eds) Click chemistry in glycoscience, new development and strategies. Willey, Hoboken, pp 33–43

    Chapter  Google Scholar 

  5. Yin C, Huo F, Zhang J, Martınez-Manez R, Yang Y, Haigang Lv, Li S (2013) Thiol-addition reactions and their applications in thiol recognition. Chem Soc Rev 42:6032–6059

    Google Scholar 

  6. Chen X, Zhou Y, Peng X, Yoon J (2010) Fluorescent and colorimetric probes for detection of thiols. Chem Soc Rev 39:2120–2135

    Article  CAS  Google Scholar 

  7. Shiu H-Y, Chong H-C, Leung Y-C, Wong MK, Che C-M (2010) A highly selective FRET-based fluorescent probe for detection of cysteine and homocysteine. Chem Eur J 16:3308–3313

    Google Scholar 

  8. Huo FJ, Sun Y-Q, Jing Su J, Yang Y-T, Yin C-X, Chao J-B (2010) Chromene “Lock”, Thiol “Key”, and Mercury (II) Ion “Hand”: a single molecular machine recognition system. Org Lett 12:4756–4759

    Google Scholar 

  9. Clayden J, MacLellan P (2011) Asymmetric synthesis of tertiary thiols and thioethers. Beilstein J Org Chem 7:582–595

    Article  CAS  Google Scholar 

  10. Khatik GL, Kumar R, Chakraborti AK (2006) Catalyst-free conjugated addition of thiols to α-β-unsaturated carbonyl compounds in water Org. Lett 8:2433–2436

    CAS  Google Scholar 

  11. Reddy VP, Kumar AV, Swapna K, Rao KR (2009) Nanoindium oxide as recyclable catalyst for C-S cross-coupling of thiols with aryl halides under ligand free conditions Org Lett 11:1697–1700

    Google Scholar 

  12. Li S, Lu Z, Meng L, Wang J (2016) Iridium-catalyzed asymmetric addition of thiophenols to oxabenzonorbornadienes Org Lett 18:5276–5279

    Google Scholar 

  13. Brachet E, Brion J-D, Messaoudi S, Alami M (2013) Palladium-catalyzed cross-coupling reaction of thioglycosides with (hetero)aryl halides Adv. Synth Catal 355:477–490

    Article  CAS  Google Scholar 

  14. Brachet E, Brion J-D, Alami M, Messaoudi S (2013) Stereoselective palladium-catalyzed alkenylation and alkynylation of thioglycosides Adv. Synth Catal 355:2627–2636

    Article  CAS  Google Scholar 

  15. Mandal PK, Maiti GH, Misra AK (2008) Catalyst-free efficient synthesis of 3-thio-2-Deoxysugar derivatives in water. J Carb Chem 27:238–257

    Article  CAS  Google Scholar 

  16. Mukherjee C, Misra AK (2007) Odorless preparation of thioglycosides and thio Michael adducts of carbohydrate derivative. J Carb Chem 26:213–221

    Article  CAS  Google Scholar 

  17. Krohn K, Ahmed I, Gehle D, Al Sahli M (2009) Open chain chiral macrolide building blocks by opening of deoxygenated 1,6-Anhydrosugars with 1,3-Propanedithiol. J Carb Chem 28:238–257

    Article  Google Scholar 

  18. Joshi G, Anslyn EV (2012) Dynamic thiol exchange with β-sulfido-α, β-unsaturated carbonyl compounds and dithianes. Org Lett 14:4714–4717

    Article  CAS  Google Scholar 

  19. Diehl KL, Kolesnichenko IV, Robotham SA, Bachman JL, Zhong Y, Brodbelt JS, Anslyn EV (2016) Click and chemically triggered declick reactions through reversible amine and thiol coupling via a conjugate acceptor. Nat Chem 8:968–973

    Article  CAS  Google Scholar 

  20. Shi B, Greaney MF (2005) Reversible Michael addition of thiols as a new tool for dynamic combinatorial chemistry. Chem Commun 886–888

    Google Scholar 

  21. Otto S, Furlan RLE, Sanders JKM (2002) Selection and amplification of hosts from dynamic combinatorial libraries of macrocyclic disulfides. Science 297:590–593

    Article  CAS  Google Scholar 

  22. Rim C, Lahey LJ, Patel VG, Zhang H, Son DY (2009) Thiol-ene reactions of 1,3,5-triacryloylhexahydro-1,3,5-triazine (TAT): facile access to functional tripodal thioethers. Tetrahedron Lett 50:745–747

    Article  CAS  Google Scholar 

  23. Højfeldt JW, Blakskjaer P, Gothelf KV (2006) A cleavable amino-thiol linker for reversible linking of amines to DNA. J Org Chem 71:9556–9559

    Article  Google Scholar 

  24. Schumacher FF, Nobles M, Ryan CP, Smith MEB, Tinker A, Caddick S, Baker JR (2011) In situ maleimide bridging of disulfides and a new approach to protein PEGylation. Bioconjug Chem 22:132–136

    Article  CAS  Google Scholar 

  25. Shi B, Stevenson R, Campopiano DJ, Greaney MF (2006) Discovery of glutathione S-transferase inhibitors using dynamic combinatorial chemistry. J Am Chem Soc 128:8459–8467

    Article  CAS  Google Scholar 

  26. Shiu H-Y, Chan T-Y, Ho C-M, Liu Y, Wong M-K, Che C-M (2009) Electron-deficient alkynes as cleavable reagents for the modification of cysteine-containing peptides in aqueous medium. Chem Eur J 15:3839–3850

    Google Scholar 

  27. Fiore M, Chambery A, Marra A, Dondoni A (2009) Single and dual glycoside clustering around calix [4] arene scaffolds via click thiol-ene coupling and azide-alkyne cycloaddition Org. Biomol Chem 7:3910–3913

    Article  CAS  Google Scholar 

  28. Conte ML, Pacifico S, Chambery A, Marra A, Dondoni A (2010) Photoinduced addition of glycosyl thiols to alkynyl peptides: use of free-radical thiol-yne coupling for post-translational double glycosylation of peptides. J Org Chem 75:4644–4647

    Article  Google Scholar 

  29. Dondoni A, Marra A (2012) Recent applications of thiol-ene coupling as a click process for glycoconjugation. Chem Soc Rev 41:573–586

    Article  CAS  Google Scholar 

  30. Dondoni A (2011) Multi-molecule reaction of serum albumin can occur through thiol-yne coupling. Chem Commun 47:11086–11088

    Article  Google Scholar 

  31. Massi A, Nanni D (2012) Thiol-yne coupling; revisiting old concepts as a breakthrough for up-to date applications Org. Biomol Chem 10:3791–3807

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Department of Pharmaceutical Sciences, Nesbitt School of Pharmacy, Wilkes University, 84 W. S. Street, Wilkes-Barre, PA, 18766, USA

    Zbigniew J. Witczak & Roman Bielski

Authors
  1. Zbigniew J. Witczak
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  2. Roman Bielski
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Correspondence to Zbigniew J. Witczak .

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Editors and Affiliations

  1. Pharmaceutical Sciences Department, Wilkes University, Wilkes-Barre, Pennsylvania, USA

    Zbigniew J. Witczak

  2. Pharmaceutical Sciences Department, Nesbitt School of Pharmacy, Wilkes University, Wilkes-Barre, Pennsylvania, USA

    Roman Bielski

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Witczak, Z.J., Bielski, R. (2018). Recognition of Thiols in Coupling Reactions to Organic and Carbohydrate Acceptors. In: Witczak, Z., Bielski, R. (eds) Coupling and Decoupling of Diverse Molecular Units in Glycosciences. Springer, Cham. https://doi.org/10.1007/978-3-319-65587-1_7

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