메뉴 건너뛰기




Volumn 9, Issue 4, 2014, Pages 880-883

A Key n→π* interaction in N -acyl homoserine lactones

Author keywords

[No Author keywords available]

Indexed keywords

CARBONYL DERIVATIVE; N ACYLHOMOSERINE LACTONE; OXYGEN; RECEPTOR; GAMMA BUTYROLACTONE DERIVATIVE;

EID: 84899094486     PISSN: 15548929     EISSN: 15548937     Source Type: Journal    
DOI: 10.1021/cb500022u     Document Type: Article
Times cited : (61)

References (45)
  • 1
    • 0032900272 scopus 로고    scopus 로고
    • Quorum sensing: The explanation of a curious phenomenon reveals a common characteristic of bacteria
    • Hastings, J. W. and Greenberg, E. P. (1999) Quorum sensing: The explanation of a curious phenomenon reveals a common characteristic of bacteria J. Bacteriol. 181, 2667-2668
    • (1999) J. Bacteriol. , vol.181 , pp. 2667-2668
    • Hastings, J.W.1    Greenberg, E.P.2
  • 2
    • 27944442272 scopus 로고    scopus 로고
    • Quorum sensing: Cell-to-cell communication in bacteria
    • Waters, C. M. and Bassler, B. L. (2005) Quorum sensing: Cell-to-cell communication in bacteria Annu. Rev. Cell Dev. Biol. 21, 319-346
    • (2005) Annu. Rev. Cell Dev. Biol. , vol.21 , pp. 319-346
    • Waters, C.M.1    Bassler, B.L.2
  • 4
    • 0035675837 scopus 로고    scopus 로고
    • Regulation of gene expression by cell-to-cell communication: Acyl-homoserine lactone quorum sensing
    • Fuqua, C., Parsek, M. R., and Greenberg, E. P. (2001) Regulation of gene expression by cell-to-cell communication: Acyl-homoserine lactone quorum sensing Annu. Rev. Genet. 35, 439-468
    • (2001) Annu. Rev. Genet. , vol.35 , pp. 439-468
    • Fuqua, C.1    Parsek, M.R.2    Greenberg, E.P.3
  • 5
    • 73349114916 scopus 로고    scopus 로고
    • Baterial quorum-sensing network architectures
    • Ng, W.-L. and Bassler, B. L. (2009) Baterial quorum-sensing network architectures Annu. Rev. Genet. 43, 197-222
    • (2009) Annu. Rev. Genet. , vol.43 , pp. 197-222
    • Ng, W.-L.1    Bassler, B.L.2
  • 6
    • 78651399983 scopus 로고    scopus 로고
    • Structural basis of acyl-homoserine lactone-dependent signaling
    • Churchill, M. E. A. and Chen, L. (2011) Structural basis of acyl-homoserine lactone-dependent signaling Chem. Rev. 111, 68-85
    • (2011) Chem. Rev. , vol.111 , pp. 68-85
    • Churchill, M.E.A.1    Chen, L.2
  • 7
    • 33644849230 scopus 로고    scopus 로고
    • Quorum-sensing inhibitors as anti-pathogenic drugs
    • Rasmussen, T. B. and Givskov, M. (2006) Quorum-sensing inhibitors as anti-pathogenic drugs Int. J. Med. Microbiol. 296, 149-161
    • (2006) Int. J. Med. Microbiol. , vol.296 , pp. 149-161
    • Rasmussen, T.B.1    Givskov, M.2
  • 8
    • 0038245117 scopus 로고    scopus 로고
    • An electronic effect on protein structure
    • Hinderaker, M. P. and Raines, R. T. (2003) An electronic effect on protein structure Protein Sci. 12, 1188-1194
    • (2003) Protein Sci. , vol.12 , pp. 1188-1194
    • Hinderaker, M.P.1    Raines, R.T.2
  • 9
    • 67650547528 scopus 로고    scopus 로고
    • Nature of amide carbonyl-carbonyl interactions in proteins
    • Choudhary, A., Gandla, D., Krow, G. R., and Raines, R. T. (2009) Nature of amide carbonyl-carbonyl interactions in proteins J. Am. Chem. Soc. 131, 7244-7246
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 7244-7246
    • Choudhary, A.1    Gandla, D.2    Krow, G.R.3    Raines, R.T.4
  • 10
    • 0001135446 scopus 로고
    • Chemical reaction paths. IV. Aspects of O···C - O interactions in crystals
    • Bürgi, H. D., Dunitz, J. D., and Shefter, E. (1974) Chemical reaction paths. IV. Aspects of O···C - O interactions in crystals Acta Crystallogr. B30, 1517-1527
    • (1974) Acta Crystallogr. , vol.30 , pp. 1517-1527
    • Bürgi, H.D.1    Dunitz, J.D.2    Shefter, E.3
  • 11
    • 84878383832 scopus 로고    scopus 로고
    • N→π* Interactions of amides and thioamides: Implications for protein stability
    • Newberry, R. W., VanVeller, B., Guzei, I. A., and Raines, R. T. (2013) n→π* Interactions of amides and thioamides: Implications for protein stability J. Am. Chem. Soc. 135, 7843-7846
    • (2013) J. Am. Chem. Soc. , vol.135 , pp. 7843-7846
    • Newberry, R.W.1    Vanveller, B.2    Guzei, I.A.3    Raines, R.T.4
  • 13
    • 77957975318 scopus 로고    scopus 로고
    • The role of Bürgi-Dunitz interactions in the structural stability of proteins
    • Fufezan, C. (2010) The role of Bürgi-Dunitz interactions in the structural stability of proteins Proteins 78, 2831-2838
    • (2010) Proteins , vol.78 , pp. 2831-2838
    • Fufezan, C.1
  • 16
    • 79956189741 scopus 로고    scopus 로고
    • Signature of n→π* interactions in α-helices
    • Choudhary, A. and Raines, R. T. (2011) Signature of n→π* interactions in α-helices Protein Sci. 20, 1077-1081
    • (2011) Protein Sci. , vol.20 , pp. 1077-1081
    • Choudhary, A.1    Raines, R.T.2
  • 17
    • 34547491911 scopus 로고    scopus 로고
    • Local and tunable n→π* interactions regulate amide isomerism in the peptoid backbone
    • Gorske, B. C., Bastian, B. L., Geske, G. D., and Blackwell, H. E. (2007) Local and tunable n→π* interactions regulate amide isomerism in the peptoid backbone J. Am. Chem. Soc. 129, 8928-8929
    • (2007) J. Am. Chem. Soc. , vol.129 , pp. 8928-8929
    • Gorske, B.C.1    Bastian, B.L.2    Geske, G.D.3    Blackwell, H.E.4
  • 18
    • 70450177277 scopus 로고    scopus 로고
    • New strategies for the design of folded peptoids revealed by a survey of noncovalent interactions in model systems
    • Gorske, B. C., Stringer, J. R., Bastian, B. L., Fowler, S. A., and Blackwell, H. E. (2009) New strategies for the design of folded peptoids revealed by a survey of noncovalent interactions in model systems J. Am. Chem. Soc. 131, 16555-16567
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 16555-16567
    • Gorske, B.C.1    Stringer, J.R.2    Bastian, B.L.3    Fowler, S.A.4    Blackwell, H.E.5
  • 19
    • 77956552715 scopus 로고    scopus 로고
    • Construction of peptoids with all trans-amide backbones and peptoid reverse turns via the tactical incorporation of N -aryl side chains capable of hydrogen bonding
    • Stringer, J. R., Crapster, J. A., Guzei, I. A., and Blackwell, H. E. (2010) Construction of peptoids with all trans-amide backbones and peptoid reverse turns via the tactical incorporation of N -aryl side chains capable of hydrogen bonding J. Org. Chem. 75, 6068-6078
    • (2010) J. Org. Chem. , vol.75 , pp. 6068-6078
    • Stringer, J.R.1    Crapster, J.A.2    Guzei, I.A.3    Blackwell, H.E.4
  • 20
    • 84874057600 scopus 로고    scopus 로고
    • Cis-trans amide bond rotamers in -peptoids and peptoids: Evaluation of stereoelectronic effects in backbone and side chains
    • Laursen, J. S., Engel-Andreasen, J., Fristrup, P., Harris, P., and Olsen, C. A. (2013) Cis-trans amide bond rotamers in -peptoids and peptoids: Evaluation of stereoelectronic effects in backbone and side chains J. Am. Chem. Soc. 135, 2835-2844
    • (2013) J. Am. Chem. Soc. , vol.135 , pp. 2835-2844
    • Laursen, J.S.1    Engel-Andreasen, J.2    Fristrup, P.3    Harris, P.4    Olsen, C.A.5
  • 21
    • 84881442942 scopus 로고    scopus 로고
    • N→π* Interactions in poly(lactic acid) suggest a role in protein folding
    • Newberry, R. W. and Raines, R. T. (2013) n→π* Interactions in poly(lactic acid) suggest a role in protein folding Chem. Commun. 49, 7699-7701
    • (2013) Chem. Commun. , vol.49 , pp. 7699-7701
    • Newberry, R.W.1    Raines, R.T.2
  • 22
    • 80054103043 scopus 로고    scopus 로고
    • An n→π* interaction in aspirin: Implications for structure and reactivity
    • Choudhary, A., Kamer, K. J., and Raines, R. T. (2011) An n→π* interaction in aspirin: Implications for structure and reactivity J. Org. Chem. 76, 7933-7937
    • (2011) J. Org. Chem. , vol.76 , pp. 7933-7937
    • Choudhary, A.1    Kamer, K.J.2    Raines, R.T.3
  • 23
    • 84874582783 scopus 로고    scopus 로고
    • Intimate interactions with carbonyl groups: Dipole-dipole or n→π
    • Kamer, K. J., Choudhary, A., and Raines, R. T. (2013) Intimate interactions with carbonyl groups: Dipole-dipole or n→π J. Org. Chem. 78, 2099-2103
    • (2013) J. Org. Chem. , vol.78 , pp. 2099-2103
    • Kamer, K.J.1    Choudhary, A.2    Raines, R.T.3
  • 24
    • 33750986797 scopus 로고    scopus 로고
    • The "azido gauche effect" - Implications for the conformation of azidoprolines
    • Sonntag, L.-S., Schweizer, S., Ochsenfeld, C., and Wennemers, H. (2006) The "azido gauche effect" - implications for the conformation of azidoprolines J. Am. Chem. Soc. 128, 14697-14703
    • (2006) J. Am. Chem. Soc. , vol.128 , pp. 14697-14703
    • Sonntag, L.-S.1    Schweizer, S.2    Ochsenfeld, C.3    Wennemers, H.4
  • 25
    • 69249155999 scopus 로고    scopus 로고
    • Stereoelectronic effects on the transition barrier of polyproline conformational interconversion
    • Chiang, Y.-C., Lin, Y.-J., and Horng, J.-C. (2009) Stereoelectronic effects on the transition barrier of polyproline conformational interconversion Protein Sci. 18, 1967-1977
    • (2009) Protein Sci. , vol.18 , pp. 1967-1977
    • Chiang, Y.-C.1    Lin, Y.-J.2    Horng, J.-C.3
  • 26
    • 77956055128 scopus 로고    scopus 로고
    • Tuning the cis/trans conformer ratio of Xaa-Pro amide bonds by intramolecular hydrogen bonds: The effect on PPII helix stability
    • Kuemin, M., Nagel, Y. A., Schweizer, S., Monnard, F. W., Ochsenfeld, C., and Wennemers, H. (2010) Tuning the cis/trans conformer ratio of Xaa-Pro amide bonds by intramolecular hydrogen bonds: The effect on PPII helix stability Angew. Chem., Int. Ed. 49, 6324-6327
    • (2010) Angew. Chem., Int. Ed. , vol.49 , pp. 6324-6327
    • Kuemin, M.1    Nagel, Y.A.2    Schweizer, S.3    Monnard, F.W.4    Ochsenfeld, C.5    Wennemers, H.6
  • 27
    • 77952351948 scopus 로고    scopus 로고
    • N→π* Interaction and n)(π Pauli repulsion are antagonistic for protein stability
    • Jakobsche, C. E., Choudhary, A., Miller, S. J., and Raines, R. T. (2010) n→π* Interaction and n)(π Pauli repulsion are antagonistic for protein stability J. Am. Chem. Soc. 132, 6651-6653
    • (2010) J. Am. Chem. Soc. , vol.132 , pp. 6651-6653
    • Jakobsche, C.E.1    Choudhary, A.2    Miller, S.J.3    Raines, R.T.4
  • 28
    • 79960387273 scopus 로고    scopus 로고
    • Quantum mechanical origin of the conformational preferences of 4-thiaproline and its S -oxides
    • Choudhary, A., Pua, K. H., and Raines, R. T. (2011) Quantum mechanical origin of the conformational preferences of 4-thiaproline and its S -oxides Amino Acids 41, 181-186
    • (2011) Amino Acids , vol.41 , pp. 181-186
    • Choudhary, A.1    Pua, K.H.2    Raines, R.T.3
  • 29
    • 79751472553 scopus 로고    scopus 로고
    • An investigation into the origin of the dramatically reduced reactivity of peptide-prolyl-thioesters in native chemical ligation
    • Pollock, S. B. and Kent, S. B. H. (2011) An investigation into the origin of the dramatically reduced reactivity of peptide-prolyl-thioesters in native chemical ligation Chem. Commun. 47, 2342-2344
    • (2011) Chem. Commun. , vol.47 , pp. 2342-2344
    • Pollock, S.B.1    Kent, S.B.H.2
  • 30
    • 79960269728 scopus 로고    scopus 로고
    • Importance of ring puckering versus interstrand hydrogen bonds for the conformational stability of collagen
    • Erdmann, R. S. and Wennemers, H. (2011) Importance of ring puckering versus interstrand hydrogen bonds for the conformational stability of collagen Angew. Chem., Int. Ed. 50, 6835-6838
    • (2011) Angew. Chem., Int. Ed. , vol.50 , pp. 6835-6838
    • Erdmann, R.S.1    Wennemers, H.2
  • 31
    • 84863624104 scopus 로고    scopus 로고
    • Origin of enantioselectivity in benzotetramisole-catalyzed dynamic kinetic resolution of azlactones
    • Liu, P., Yang, X., Birman, V. B., and Houk, K. N. (2012) Origin of enantioselectivity in benzotetramisole-catalyzed dynamic kinetic resolution of azlactones Org. Lett. 14, 3288-3291
    • (2012) Org. Lett. , vol.14 , pp. 3288-3291
    • Liu, P.1    Yang, X.2    Birman, V.B.3    Houk, K.N.4
  • 32
    • 84864055190 scopus 로고    scopus 로고
    • A method for stabilizing the cis prolyl peptide bond: Influence of an unusual n→π* interaction in 1,3-oxazine and 1,3-thiazine containing peptidomimetics
    • Reddy, D. N., Thirupathi, R., Tumminakatti, S., and Prabhakaran, E. N. (2012) A method for stabilizing the cis prolyl peptide bond: Influence of an unusual n→π* interaction in 1,3-oxazine and 1,3-thiazine containing peptidomimetics Tetrahedron Lett. 53, 4413-4417
    • (2012) Tetrahedron Lett. , vol.53 , pp. 4413-4417
    • Reddy, D.N.1    Thirupathi, R.2    Tumminakatti, S.3    Prabhakaran, E.N.4
  • 33
    • 84866675215 scopus 로고    scopus 로고
    • Origins of stereoselectivities of dihydroxylations of cis-bicyclo[3.3.0]octenes
    • Wang, H., Kohler, P., Overman, L. E., and Houk, K. N. (2012) Origins of stereoselectivities of dihydroxylations of cis-bicyclo[3.3.0]octenes J. Am. Chem. Soc. 134, 16054-16058
    • (2012) J. Am. Chem. Soc. , vol.134 , pp. 16054-16058
    • Wang, H.1    Kohler, P.2    Overman, L.E.3    Houk, K.N.4
  • 34
    • 0039433935 scopus 로고
    • The nature of the chemical bond. III. The transition from one extreme bond type to another
    • Pauling, L. (1932) The nature of the chemical bond. III. The transition from one extreme bond type to another J. Am. Chem. Soc. 54, 988-1003
    • (1932) J. Am. Chem. Soc. , vol.54 , pp. 988-1003
    • Pauling, L.1
  • 35
    • 0003438540 scopus 로고
    • Cornell University Press, Ithaca, NY.
    • Pauling, L. (1939) in The Nature of the Chemical Bond, pp 186-193, Cornell University Press, Ithaca, NY.
    • (1939) The Nature of the Chemical Bond , pp. 186-193
    • Pauling, L.1
  • 36
    • 0011083499 scopus 로고
    • Intermolecular interactions from a natural bond orbital, donor-acceptor viewpoint
    • Reed, A. E., Curtiss, L. A., and Weinhold, F. (1988) Intermolecular interactions from a natural bond orbital, donor-acceptor viewpoint Chem. Rev. 88, 899-926
    • (1988) Chem. Rev. , vol.88 , pp. 899-926
    • Reed, A.E.1    Curtiss, L.A.2    Weinhold, F.3
  • 40
    • 84856144512 scopus 로고    scopus 로고
    • Modulation of an n→π* interaction with α-fluoro groups
    • Choudhary, A., Fry, C. G., and Raines, R. T. (2010) Modulation of an n→π* interaction with α-fluoro groups ARKIVOC 251-262
    • (2010) ARKIVOC , pp. 251-262
    • Choudhary, A.1    Fry, C.G.2    Raines, R.T.3
  • 41
    • 49049149248 scopus 로고
    • Study of hydrolysis of amido-substituted butyrolactones by pH-stat titration and ultraviolet spectroscopic analyses
    • Rackham, D. M., Chakrabarti, J. K., and Davies, G. L. O. (1981) Study of hydrolysis of amido-substituted butyrolactones by pH-stat titration and ultraviolet spectroscopic analyses Talanta 28, 329-331
    • (1981) Talanta , vol.28 , pp. 329-331
    • Rackham, D.M.1    Chakrabarti, J.K.2    Davies, G.L.O.3
  • 42
    • 0036785621 scopus 로고    scopus 로고
    • N -Acylhomoserine lactones undergo lactonolysis in a pH-, temperature-, and acyl chain length-dependent manner during growth of Yersinia pseudotuberculosis and Pseudomonas aeruginos
    • Yates, E. A., Philipp, B., Buckley, C., Atkinson, S., Chhabra, S. R., Sockett, R. E., Goldner, M., Dessaux, Y., Cámara, M., Smith, H., and Williams, P. (2002) N -Acylhomoserine lactones undergo lactonolysis in a pH-, temperature-, and acyl chain length-dependent manner during growth of Yersinia pseudotuberculosis and Pseudomonas aeruginos Infect. Immun. 70, 5635-5646
    • (2002) Infect. Immun. , vol.70 , pp. 5635-5646
    • Yates, E.A.1    Philipp, B.2    Buckley, C.3    Atkinson, S.4    Chhabra, S.R.5    Sockett, R.E.6    Goldner, M.7    Dessaux, Y.8    Cámara, M.9    Smith, H.10    Williams, P.11
  • 44
    • 84882601735 scopus 로고    scopus 로고
    • An n→π* interaction reduces the electrophilicity of the acceptor carbonyl group
    • Choudhary, A., Fry, C. G., Kamer, K. J., and Raines, R. T. (2013) An n→π* interaction reduces the electrophilicity of the acceptor carbonyl group Chem. Commun. 49, 8166-8168
    • (2013) Chem. Commun. , vol.49 , pp. 8166-8168
    • Choudhary, A.1    Fry, C.G.2    Kamer, K.J.3    Raines, R.T.4
  • 45
    • 35948991561 scopus 로고    scopus 로고
    • Modulation of bacterial quorum sensing with synthetic ligands: Systematic evaluation of N -acylated homoserine lactones in multiple species and new insights into their mechanisms of action
    • Geske, G. D., O'Neill, J. C., Miller, D. M., Mattmann, M. E., and Blackwell, H. E. (2007) Modulation of bacterial quorum sensing with synthetic ligands: Systematic evaluation of N -acylated homoserine lactones in multiple species and new insights into their mechanisms of action J. Am. Chem. Soc. 129, 13613-13625
    • (2007) J. Am. Chem. Soc. , vol.129 , pp. 13613-13625
    • Geske, G.D.1    O'Neill, J.C.2    Miller, D.M.3    Mattmann, M.E.4    Blackwell, H.E.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.