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Volumn 9, Issue 11, 2014, Pages 2563-2571

Aldehyde recognition and discrimination by mammalian odorant receptors via functional group-specific hydration chemistry

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; G PROTEIN COUPLED RECEPTOR; ODORANT RECEPTOR; RECEPTOR; UNCLASSIFIED DRUG; WATER; OLFACTORY RECEPTOR;

EID: 84913598349     PISSN: 15548929     EISSN: 15548937     Source Type: Journal    
DOI: 10.1021/cb400290u     Document Type: Article
Times cited : (21)

References (51)
  • 1
    • 78049508421 scopus 로고    scopus 로고
    • The cell biology of smell
    • DeMaria, S., and Ngai, J. (2010) The cell biology of smell. J. Cell Biol. 191, 443-452.
    • (2010) J. Cell Biol. , vol.191 , pp. 443-452
    • DeMaria, S.1    Ngai, J.2
  • 2
    • 0035855833 scopus 로고    scopus 로고
    • How the olfactory system makes sense of scents
    • Firestein, S. (2001) How the olfactory system makes sense of scents. Nature 413, 211-218.
    • (2001) Nature , vol.413 , pp. 211-218
    • Firestein, S.1
  • 3
    • 0027981484 scopus 로고
    • Allelic inactivation regulates olfactory receptor gene expression
    • Chess, A., Simon, I., Cedar, H., and Axel, R. (1994) Allelic inactivation regulates olfactory receptor gene expression. Cell 78, 823-834.
    • (1994) Cell , vol.78 , pp. 823-834
    • Chess, A.1    Simon, I.2    Cedar, H.3    Axel, R.4
  • 4
    • 0033525727 scopus 로고    scopus 로고
    • Combinatorial receptor codes for odors
    • Malnic, B., Hirono, J., Sato, T., and Buck, L. B. (1999) Combinatorial receptor codes for odors. Cell 96, 713-723.
    • (1999) Cell , vol.96 , pp. 713-723
    • Malnic, B.1    Hirono, J.2    Sato, T.3    Buck, L.B.4
  • 5
    • 14744284850 scopus 로고    scopus 로고
    • Evolutionary changes of the number of olfactory receptor genes in the human and mouse lineages
    • Niimura, Y., and Nei, M. (2005) Evolutionary changes of the number of olfactory receptor genes in the human and mouse lineages. Gene 346, 23-28.
    • (2005) Gene , vol.346 , pp. 23-28
    • Niimura, Y.1    Nei, M.2
  • 6
    • 0036163689 scopus 로고    scopus 로고
    • The olfactory receptor gene superfamily of the mouse
    • Zhang, X., and Firestein, S. (2002) The olfactory receptor gene superfamily of the mouse. Nat. Neurosci. 5, 124-133.
    • (2002) Nat. Neurosci. , vol.5 , pp. 124-133
    • Zhang, X.1    Firestein, S.2
  • 7
    • 33947149178 scopus 로고    scopus 로고
    • Comparative genomics of odorant and pheromone receptor genes in rodents
    • Zhang, X., Zhang, X., and Firestein, S. (2007) Comparative genomics of odorant and pheromone receptor genes in rodents. Genomics 89, 441-450.
    • (2007) Genomics , vol.89 , pp. 441-450
    • Zhang, X.1    Zhang, X.2    Firestein, S.3
  • 10
    • 14044270215 scopus 로고    scopus 로고
    • Structural basis for a broad but selective ligand spectrum of a mouse olfactory receptor: Mapping the odorant-binding site
    • Katada, S., Hirokawa, T., Oka, Y., Suwa, M., and Touhara, K. (2005) Structural basis for a broad but selective ligand spectrum of a mouse olfactory receptor: Mapping the odorant-binding site. J. Neurosci. 25, 1806-1815.
    • (2005) J. Neurosci. , vol.25 , pp. 1806-1815
    • Katada, S.1    Hirokawa, T.2    Oka, Y.3    Suwa, M.4    Touhara, K.5
  • 11
    • 33646564061 scopus 로고    scopus 로고
    • Synthesis and olfactory properties of 2-alkanals, analogues of 2-methylundecanal
    • Gibka, J., and Glinski, M. (2006) Synthesis and olfactory properties of 2-alkanals, analogues of 2-methylundecanal. Flavour Fragrance J. 21, 480-483.
    • (2006) Flavour Fragrance J. , vol.21 , pp. 480-483
    • Gibka, J.1    Glinski, M.2
  • 12
    • 79959701933 scopus 로고    scopus 로고
    • The human olfactory receptor 17-40: Requisites for fitting into the binding pocket
    • Anselmi, C., Buonocore, A., Centini, M., Facino, R. M., and Hatt, H. (2011) The human olfactory receptor 17-40: Requisites for fitting into the binding pocket. Comput. Biol. Chem. 35, 159-168.
    • (2011) Comput. Biol. Chem. , vol.35 , pp. 159-168
    • Anselmi, C.1    Buonocore, A.2    Centini, M.3    Facino, R.M.4    Hatt, H.5
  • 13
    • 79952084703 scopus 로고    scopus 로고
    • The mouse eugenol odorant receptor: Structural and functional plasticity of a broadly tuned odorant binding pocket
    • Baud, O., Etter, S., Spreafico, M., Bordoli, L., Schwede, T., Vogel, H., and Pick, H. (2011) The mouse eugenol odorant receptor: Structural and functional plasticity of a broadly tuned odorant binding pocket. Biochemistry 50, 843-853.
    • (2011) Biochemistry , vol.50 , pp. 843-853
    • Baud, O.1    Etter, S.2    Spreafico, M.3    Bordoli, L.4    Schwede, T.5    Vogel, H.6    Pick, H.7
  • 14
    • 84870671969 scopus 로고    scopus 로고
    • How broadly tuned olfactory receptors equally recognize their agonists. Human OR1G1 as a test case
    • Charlier, L., Topin, J., Ronin, C., Kim, S. K., Goddard, W. A., 3rd, Efremov, R., and Golebiowski, J. (2012) How broadly tuned olfactory receptors equally recognize their agonists. Human OR1G1 as a test case. Cell. Mol. Life Sci. 69, 4205-4213.
    • (2012) Cell. Mol. Life Sci. , vol.69 , pp. 4205-4213
    • Charlier, L.1    Topin, J.2    Ronin, C.3    Kim, S.K.4    Goddard, W.A.5    Efremov, R.6    Golebiowski, J.7
  • 15
    • 34250824718 scopus 로고    scopus 로고
    • Prediction of perception: Probing the hOR17-4 olfactory receptor model with silicon analogues of bourgeonal and lilial
    • Doszczak, L., Kraft, P., Weber, H. P., Bertermann, R., Triller, A., Hatt, H., and Tacke, R. (2007) Prediction of perception: Probing the hOR17-4 olfactory receptor model with silicon analogues of bourgeonal and lilial. Angew. Chem., Int. Ed. Engl. 46, 3367-3371.
    • (2007) Angew. Chem., Int. Ed. Engl. , vol.46 , pp. 3367-3371
    • Doszczak, L.1    Kraft, P.2    Weber, H.P.3    Bertermann, R.4    Triller, A.5    Hatt, H.6    Tacke, R.7
  • 16
    • 14144249986 scopus 로고    scopus 로고
    • Predicted 3-D structures for mouse I7 and rat I7 olfactory receptors and comparison of predicted odor recognition profiles with experiment
    • Hall, S. E., Floriano, W. B., Vaidehi, N., and Goddard, W. A., 3rd (2004) Predicted 3-D structures for mouse I7 and rat I7 olfactory receptors and comparison of predicted odor recognition profiles with experiment. Chem. Senses 29, 595-616.
    • (2004) Chem. Senses , vol.29 , pp. 595-616
    • Hall, S.E.1    Floriano, W.B.2    Vaidehi, N.3    Goddard, W.A.4
  • 19
    • 27944475233 scopus 로고    scopus 로고
    • Structural activation pathways from dynamic olfactory receptor-odorant interactions
    • Lai, P. C., Singer, M. S., and Crasto, C. J. (2005) Structural activation pathways from dynamic olfactory receptor-odorant interactions. Chem. Senses 30, 781-792.
    • (2005) Chem. Senses , vol.30 , pp. 781-792
    • Lai, P.C.1    Singer, M.S.2    Crasto, C.J.3
  • 23
    • 0034042247 scopus 로고    scopus 로고
    • Analysis of the molecular basis for octanal interactions in the expressed rat 17 olfactory receptor
    • Singer, M. S. (2000) Analysis of the molecular basis for octanal interactions in the expressed rat 17 olfactory receptor. Chem. Senses 25, 155-165.
    • (2000) Chem. Senses , vol.25 , pp. 155-165
    • Singer, M.S.1
  • 25
    • 84913528193 scopus 로고
    • The reversible hydration of carbonyl compounds in aqueous solution. Part II: The kinetics of the keto/gem-diol transition
    • Buschmann, H.-J., Dutkiewicsz, E., and Knoche, W. (1982) The reversible hydration of carbonyl compounds in aqueous solution. Part II: The kinetics of the keto/gem-diol transition. Ber. Bunsen-Ges. Phys. Chem. Chem. Phys. 86, 139-144.
    • (1982) Ber. Bunsen-Ges. Phys. Chem. Chem. Phys. , vol.86 , pp. 139-144
    • Buschmann, H.-J.1    Dutkiewicsz, E.2    Knoche, W.3
  • 26
    • 0002301488 scopus 로고
    • The reversible hydration of carbonyl compounds in aqueous solution. Part I: The keto/gem-diol equilibrium
    • Buschmann, H.-J., Fuldner, H.-H., and Knochem, W. (1980) The reversible hydration of carbonyl compounds in aqueous solution. Part I: The keto/gem-diol equilibrium. Ber. Bunsen-Ges. Phys. Chem. Chem. Phys. 84, 41-44.
    • (1980) Ber. Bunsen-Ges. Phys. Chem. Chem. Phys. , vol.84 , pp. 41-44
    • Buschmann, H.-J.1    Fuldner, H.-H.2    Knochem, W.3
  • 27
    • 0037333867 scopus 로고    scopus 로고
    • New fluorinated derivatives as esterase inhibitors. Synthesis, hydration, and crossed specificity studies
    • Quero, C., Rosell, G., Jimenez, O., Rodriguez, S., Bosch, M. P., and Guerrero, A. (2003) New fluorinated derivatives as esterase inhibitors. Synthesis, hydration, and crossed specificity studies. Bioorg. Med. Chem. 11, 1047-1055.
    • (2003) Bioorg. Med. Chem. , vol.11 , pp. 1047-1055
    • Quero, C.1    Rosell, G.2    Jimenez, O.3    Rodriguez, S.4    Bosch, M.P.5    Guerrero, A.6
  • 28
    • 1642524949 scopus 로고    scopus 로고
    • A pharmacological profile of the aldehyde receptor repertoire in rat olfactory epithelium
    • Araneda, R. C., Peterlin, Z., Zhang, X., Chesler, A., and Firestein, S. (2004) A pharmacological profile of the aldehyde receptor repertoire in rat olfactory epithelium. J. Physiol. 555, 743-756.
    • (2004) J. Physiol. , vol.555 , pp. 743-756
    • Araneda, R.C.1    Peterlin, Z.2    Zhang, X.3    Chesler, A.4    Firestein, S.5
  • 29
    • 0034115065 scopus 로고    scopus 로고
    • Responsiveness of olfactory neurons to distinct aliphatic aldehydes
    • Kaluza, J. F., and Breer, H. (2000) Responsiveness of olfactory neurons to distinct aliphatic aldehydes. J. Exp. Biol. 203, 927-933.
    • (2000) J. Exp. Biol. , vol.203 , pp. 927-933
    • Kaluza, J.F.1    Breer, H.2
  • 30
    • 0032417641 scopus 로고    scopus 로고
    • Identification of ligands for olfactory receptors by functional expression of a receptor library
    • Krautwurst, D., Yau, K. W., and Reed, R. R. (1998) Identification of ligands for olfactory receptors by functional expression of a receptor library. Cell 95, 917-926.
    • (1998) Cell , vol.95 , pp. 917-926
    • Krautwurst, D.1    Yau, K.W.2    Reed, R.R.3
  • 31
    • 57649219010 scopus 로고    scopus 로고
    • The importance of odorant conformation to the binding and activation of a representative olfactory receptor
    • Peterlin, Z., Li, Y., Sun, G., Shah, R., Firestein, S., and Ryan, K. (2008) The importance of odorant conformation to the binding and activation of a representative olfactory receptor. Chem. Biol. 15, 1317-1327.
    • (2008) Chem. Biol. , vol.15 , pp. 1317-1327
    • Peterlin, Z.1    Li, Y.2    Sun, G.3    Shah, R.4    Firestein, S.5    Ryan, K.6
  • 32
    • 0033712368 scopus 로고    scopus 로고
    • The molecular receptive range of an odorant receptor
    • Araneda, R. C., Kini, A. D., and Firestein, S. (2000) The molecular receptive range of an odorant receptor. Nat. Neurosci. 3, 1248-1255.
    • (2000) Nat. Neurosci. , vol.3 , pp. 1248-1255
    • Araneda, R.C.1    Kini, A.D.2    Firestein, S.3
  • 33
    • 38149016915 scopus 로고    scopus 로고
    • Understanding organofluorine chemistry. An introduction to the C-F bond
    • O'Hagan, D. (2008) Understanding organofluorine chemistry. An introduction to the C-F bond. Chem. Soc. Rev. 37, 308-319.
    • (2008) Chem. Soc. Rev. , vol.37 , pp. 308-319
    • O'Hagan, D.1
  • 34
    • 20444494428 scopus 로고    scopus 로고
    • Direct asymmetric alpha-fluorination of aldehydes
    • Steiner, D. D., Mase, N., and Barbas, C. F., 3rd. (2005) Direct asymmetric alpha-fluorination of aldehydes. Angew. Chem., Int. Ed. Engl. 44, 3706-3710.
    • (2005) Angew. Chem., Int. Ed. Engl. , vol.44 , pp. 3706-3710
    • Steiner, D.D.1    Mase, N.2    Barbas, C.F.3
  • 35
    • 1642524949 scopus 로고    scopus 로고
    • A pharmacological profile of the aldehyde receptor repertoire in rat olfactory epithelium
    • Araneda, R. C., Peterlin, Z., Zhang, X., Chesler, A., and Firestein, S. (2004) A pharmacological profile of the aldehyde receptor repertoire in rat olfactory epithelium. J. Physiol. 555, 743-756.
    • (2004) J. Physiol. , vol.555 , pp. 743-756
    • Araneda, R.C.1    Peterlin, Z.2    Zhang, X.3    Chesler, A.4    Firestein, S.5
  • 36
    • 0037092426 scopus 로고    scopus 로고
    • Odorant receptor expression defines functional units in the mouse olfactory system
    • Bozza, T., Feinstein, P., Zheng, C., and Mombaerts, P. (2002) Odorant receptor expression defines functional units in the mouse olfactory system. J. Neurosci. 22, 3033-3043.
    • (2002) J. Neurosci. , vol.22 , pp. 3033-3043
    • Bozza, T.1    Feinstein, P.2    Zheng, C.3    Mombaerts, P.4
  • 38
    • 84879644900 scopus 로고    scopus 로고
    • Spontaneous and sensory-evoked activity in mouse olfactory sensory neurons with defined odorant receptors
    • Connelly, T., Savigner, A., and Ma, M. (2013) Spontaneous and sensory-evoked activity in mouse olfactory sensory neurons with defined odorant receptors. J. Neurophysiol. 110, 55-62.
    • (2013) J. Neurophysiol. , vol.110 , pp. 55-62
    • Connelly, T.1    Savigner, A.2    Ma, M.3
  • 39
    • 78651349003 scopus 로고    scopus 로고
    • Activation state of the M3 muscarinic acetylcholine receptor modulates mammalian odorant receptor signaling
    • Li, Y. R., and Matsunami, H. (2011) Activation state of the M3 muscarinic acetylcholine receptor modulates mammalian odorant receptor signaling. Sci. Signaling 4, ra1.
    • (2011) Sci. Signaling , vol.4 , pp. ra1
    • Li, Y.R.1    Matsunami, H.2
  • 40
    • 34447549293 scopus 로고    scopus 로고
    • Synergism of accessory factors in functional expression of mammalian odorant receptors
    • Zhuang, H., and Matsunami, H. (2007) Synergism of accessory factors in functional expression of mammalian odorant receptors. J. Biol. Chem. 282, 15284-15293.
    • (2007) J. Biol. Chem. , vol.282 , pp. 15284-15293
    • Zhuang, H.1    Matsunami, H.2
  • 41
    • 51649104139 scopus 로고    scopus 로고
    • Evaluating cell-surface expression and measuring activation of mammalian odorant receptors in heterologous cells
    • Zhuang, H., and Matsunami, H. (2008) Evaluating cell-surface expression and measuring activation of mammalian odorant receptors in heterologous cells. Nat. Protoc. 3, 1402-1413.
    • (2008) Nat. Protoc. , vol.3 , pp. 1402-1413
    • Zhuang, H.1    Matsunami, H.2
  • 42
    • 84865201339 scopus 로고    scopus 로고
    • Homology model-assisted elucidation of binding sites in GPCRs
    • Levit, A., Barak, D., Behrens, M., Meyerhof, W., and Niv, M. Y. (2012) Homology model-assisted elucidation of binding sites in GPCRs. Methods Mol. Biol. 914, 179-205.
    • (2012) Methods Mol. Biol. , vol.914 , pp. 179-205
    • Levit, A.1    Barak, D.2    Behrens, M.3    Meyerhof, W.4    Niv, M.Y.5
  • 44
    • 0342587083 scopus 로고
    • Kinetics of hydration of aliphatic aldehydes
    • Gruen, L. C., and McTigue, P. T. (1963) Kinetics of hydration of aliphatic aldehydes. J. Chem. Soc., 5224-5229.
    • (1963) J. Chem. Soc. , pp. 5224-5229
    • Gruen, L.C.1    McTigue, P.T.2
  • 46
    • 0014288982 scopus 로고
    • The catalytic versatility of erythrocyte carbonic anhydrase. V. Kinetic studies of enzymecatalyzed hydrations of aliphatic aldehydes
    • Pocker, Y., and Dickerson, D. G. (1968) The catalytic versatility of erythrocyte carbonic anhydrase. V. Kinetic studies of enzymecatalyzed hydrations of aliphatic aldehydes. Biochemistry 7, 1995-2004.
    • (1968) Biochemistry , vol.7 , pp. 1995-2004
    • Pocker, Y.1    Dickerson, D.G.2
  • 48
    • 78649757442 scopus 로고    scopus 로고
    • Enzymatic conversion of odorants in nasal mucus affects olfactory glomerular activation patterns and odor perception
    • Nagashima, A., and Touhara, K. (2010) Enzymatic conversion of odorants in nasal mucus affects olfactory glomerular activation patterns and odor perception. J. Neurosci. 30, 16391-16398.
    • (2010) J. Neurosci. , vol.30 , pp. 16391-16398
    • Nagashima, A.1    Touhara, K.2
  • 49
    • 0041509257 scopus 로고
    • Acid-base-catalyzed hydration of acetaldehyde. Buffer and metal ion catalysis
    • Pocker, Y., and Meany, J. E. (1967) Acid-base-catalyzed hydration of acetaldehyde. Buffer and metal ion catalysis. J. Phys. Chem. 71, 3113-&.
    • (1967) J. Phys. Chem. , vol.71 , pp. 3113
    • Pocker, Y.1    Meany, J.E.2
  • 51
    • 47049084133 scopus 로고    scopus 로고
    • Internal hydration increases during activation of the G-protein-coupled receptor rhodopsin
    • Grossfield, A., Pitman, M. C., Feller, S. E., Soubias, O., and Gawrisch, K. (2008) Internal hydration increases during activation of the G-protein-coupled receptor rhodopsin. J. Mol. Biol. 381, 478-486.
    • (2008) J. Mol. Biol. , vol.381 , pp. 478-486
    • Grossfield, A.1    Pitman, M.C.2    Feller, S.E.3    Soubias, O.4    Gawrisch, K.5


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