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Original Articles

S-Ribosylhomocysteine analogues modified at the ribosyl C-4 position

, , , , , , & show all
Pages 307-327 | Received 12 Nov 2015, Accepted 30 Dec 2015, Published online: 24 Feb 2016

References

  • Waters CM, Bassler BL. Quorum sensing: cell-to-cell communication in bacteria. Annu Rev Cell Dev Biol. 2005;21:319–346.
  • Zhu J, Kaufmann GF. Quo vadis quorum quenching? Curr Opin Pharmacol. 2013;13:688–698.
  • Pereira CS, Thompson JA, Xavier KB. AI-2-mediated signalling in bacteria. FEMS Microbiol Rev. 2013;37:156–181.
  • Kalia VC (ed.). Quorum sensing vs quorum quenching: a battle with no end in sight. New Delhi: Springer; 2015.
  • Mattmann ME, Blackwell HE. Small molecules that modulate quorum sensing and control virulence in Pseudomonas aeruginosa. J Org Chem. 2010;75:6737–6746.
  • Galloway WRJD, Hodgkinson JT, Bowden SD, Welch M, Spring DR. Quorum sensing in gram-negative bacteria: small-molecule modulation of AHL and AI-2 quorum sensing pathways. Chem Rev. 2011;111:28–67.
  • Amara N, Krom BP, Kaufmann GF, Meijler MM. Macromolecular inhibition of quorum sensing: enzymes, antibodies, and beyond. Chem Rev. 2011;111:195–208.
  • Ni N, Li M, Wang J, Wang B. Inhibitors and antagonists of bacterial quorum sensing. Med Res Rev. 2009;29:65–124.
  • Amara N, Mashiach R, Amar D, Krief P, Spieser SAH, Bottomley MJ, et al. Covalent inhibition of bacterial quorum sensing. J Am Chem Soc. 2009;131:10610–10619.
  • Clevenger KD, Fast W. ‘Clicking’ on the lights to reveal bacterial social networking. Chem Bio Chem. 2012;13:508–510.
  • The boric acid required for the complexation of DPD is available in biosphere (e.g., the concentration of boric acids in sea water is approximately 0.4 mM) (Ref. 12).
  • Chen X, Schauder S, Potier N, Van Dorsselaer A, Pelczer I, Bassler BL, et al. Structural identification of a bacterial quorum-sensing signal containing boron. Nature. 2002;415:545–549.
  • Zhu J, Hu X, Dizin E, Pei D. Catalytic mechanism of S-ribosylhomocysteinase (LuxS): direct observation of ketone intermediates by 13C NMR spectroscopy. J Am Chem Soc. 2003;125:13379–13381.
  • Globisch D, Lowery CA, McCague KC, Janda KD. Uncharacterized 4,5-dihydroxy-2,3-pentanedione (DPD) molecules revealed through NMR spectroscopy: implications for a greater signaling diversity in bacterial species. Angew Chem Int Ed. 2012;51:4204–4208.
  • Alfaro JF, Zhang T, Wynn DP, Karschner EL, Zhou ZS. Synthesis of LuxS inhibitors targeting bacterial cell-cell communication. Org Lett. 2004;6:3043–3046.
  • Malladi VLA, Sobczak AJ, Meyer TM, Pei D, Wnuk SF. Inhibition of LuxS by S-ribosylhomocysteine analogues containing a [4-Aza]ribose ring. Bioorg Med Chem. 2011;19:5507–5519.
  • Sobczak AJ, Chbib C, Wnuk SF. S-ribosylhomocysteine analogs containing a [4-thio]ribose ring. Carbohydr Res. 2015;415:39–47.
  • Wnuk SF, Robert J, Sobczak AJ, Meyers BP, Malladi VLA, Zhu J, et al. Inhibition of S-ribosylhomocysteinase (LuxS) by substrate analogues modified at the ribosyl C-3 position. Bioorg Med Chem. 2009;17:6699–6706.
  • Gopishetty B, Zhu J, Rajan R, Sobczak AJ, Wnuk SF, Bell CE, et al. Probing the catalytic mechanism of S-ribosylhomocysteinase (LuxS) with catalytic intermediates and substrate analogues. J Am Chem Soc. 2009;131:1243–1250.
  • Zang T, Lee BWK, Cannon LM, Ritter KA, Dai S, Ren D, et al. A naturally occurring brominated furanone covalently modifies and inactivates LuxS. Bioorg Med Chem Lett. 2009;19:6200–6204.
  • Liu R. Synthesis of S-Ribosyl-l -homocysteine and analogs modified at the homocysteine-C3 position. M.Sc. thesis, University of San Francisco, San Francisco, 2012.
  • Bhattacharyya M, Vishveshwara S. Functional correlation of bacterial LuxS with their quaternary associations: interface analysis of the structure networks. BMC Struct Biol. 2009;9:8.
  • Bhattacharyya M, Vishveshwara S. Elucidation of the conformational free energy landscape in H.pylori LuxS and its implications to catalysis. BMC Struct Biol. 2010;10:27.
  • Maddaford A, Guyot T, Leese D, Glen R, Hart J, Zhang X, et al. Synthesis of enantiomerically pure 4-substituted riboses. Synlett. 2007:3149–3154.
  • Johnson CR, Esker JL, Van Zandt MC. Chemoenzymic synthesis of 4-substituted riboses. S-(4′-methyladenosyl)-l-homocysteine. J Org Chem. 1994;59:5854–5855.
  • Betson M, Allanson N, Wainwright P. A review of methods to synthesise 4′-substituted nucleosides. Org Biomol Chem. 2014;12:9291–9306.
  • Since substrate 6 and products 12–19 are derivatives of D-ribose, for consitency the nomenclature for the ribitol synthetic intermediates 7–11, including 1H and 13C NMR assignments, are using ribose carbon numbering as showed in structure for 7/8. It is noteworthy that ribitols 7/8 and 10/11 can be treated as either D or L sugars (no reference point to classify them), while ketone 9 is L sugar.
  • Marco JA, Carda M, González F, Rodríguez S, Castillo E, Murga J. Diastereoselectivity in organometallic additions to the carbonyl group of protected erythrulose derivatives. J Org Chem. 1998;63:698–707.
  • Maddaford A, Wainwright P, Glen R, Fisher R, Dragovich PS, Gonzalez J, et al. Stereoselective synthesis of rac-4′-ethynyl-2′-deoxy- and 4′-ethynyl-2′,3′-dideoxy-2′,3′-didehydronucleoside analogues. Synthesis. 2007:1378–1384.
  • Bloch R, Brillet C. Selective oxidation of primary-secondary diols to lactones catalyzed by tetrapropylammonium perruthenate. Synlett. 1991:829–830.
  • Xavier NM, Rauter AP, Queneau Y. Carbohydrate-based lactones: synthesis and applications. Top Curr Chem. 2010;295:19–62.
  • The γ-lactones should provide SRH analogues with different rate of ring opening comparing to natural SRH (hemiacetal) as observed with 4-aza-SRH analogue (azahemiacetal) and the corresponding γ-lactam (Ref. 16).
  • Ley SV, Norman J, Griffith WP, Marsden SP. Tetrapropylammonium perruthenate, Pr4N+RuO4-, TPAP: a catalytic oxidant for organic synthesis. Synthesis. 1994;1994:639–666.
  • Schmidt A-KC, Stark CBW. TPAP-catalyzed direct oxidation of primary alcohols to carboxylic acids through stabilized aldehyde hydrates. Org Lett. 2011;13:4164–4167.
  • Detritylation and derivatisation of the similar C-substituted lactones was noted to be challenging most probably due to the crowded nature of the ribose skeleton (Ref. 24).
  • Stevens JD, Fletcher HG. Proton magnetic resonance spectra of pentofuranose derivatives. J Org Chem. 1968;33:1799–1805.
  • Serianni AS, Barker R. [13C]-Enriched tetroses and tetrofuranosides: an evaluation of the relationship between NMR parameters and furanosyl ring conformation. J Org Chem. 1984;49:3292–3300.
  • Zhao G, Wan W, Mansouri S, Alfaro JF, Bassler BL, Cornell KA, et al. Chemical synthesis of S-ribosyl-l-homocysteine and activity assay as a LuxS substrate. Bioorg Med Chem Lett. 2003;13:3897–3900.
  • Llewellyn DB, Wahhab A. An efficient synthesis of base-substituted analogues of S-adenosyl-dl-homocysteine. Tetrahedron Lett. 2009;50:3939–3941.
  • Bolitho ME, Corcoran BJ, Showell-Rouse EI, Wang KQ. Revisiting synthetic preparation of the quorum sensing substrate S-D-ribosyl-l-homocysteine (SRH). Carbohydr Res. 2014;394:32–38.
  • Sá MM, Silveira GP, Caroa MSB, Ellenab J. Synthesis of novel O-acylated-D-ribono-1,5-lactones and structural assignment supported by conventional Noesy-NMR and X-ray analysis. J Braz Chem Soc. 2008;19:18–23.
  • Nasomjai P, O'Hagan D, Slawin AMZ. Synthesis of phosphonate and phostone analogues of ribose-1-phosphates. Beil J Org Chem. 2009;5: No. 37. doi:10.3762/bjoc.5.37.

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