mesylates

Summary

Summary: Organic salts or esters of methanesulfonic acid.

Top Publications

  1. Bai Y, Li M, Hwang T. Structural basis for the channel function of a degraded ABC transporter, CFTR (ABCC7). J Gen Physiol. 2011;138:495-507 pubmed publisher
    ..Collectively, our data corroborate the popular hypothesis that degradation of the cytoplasmic-side gate turned an ABC transporter into the CFTR channel. ..
  2. Bhayana B, Fors B, Buchwald S. A versatile catalyst system for Suzuki-Miyaura cross-coupling reactions of C(sp(2))-tosylates and mesylates. Org Lett. 2009;11:3954-7 pubmed publisher
    A catalyst system for the Suzuki-Miyaura cross-coupling reactions of aryl and vinyl tosylates and mesylates has been developed...
  3. El Hiani Y, Linsdell P. Changes in accessibility of cytoplasmic substances to the pore associated with activation of the cystic fibrosis transmembrane conductance regulator chloride channel. J Biol Chem. 2010;285:32126-40 pubmed publisher
    ..One logical interpretation of these findings is that cytoplasmic access to residues at the narrowest region of the pore changes concomitant with activation. ..
  4. Bai Y, Li M, Hwang T. Dual roles of the sixth transmembrane segment of the CFTR chloride channel in gating and permeation. J Gen Physiol. 2010;136:293-309 pubmed publisher
    ..These results corroborate the idea that a helix rotation of TM6, which has been proposed to be part of the molecular motions during transport cycles in other ABC transporters, is associated with gating of the CFTR pore. ..
  5. Kawate T, Robertson J, Li M, Silberberg S, Swartz K. Ion access pathway to the transmembrane pore in P2X receptor channels. J Gen Physiol. 2011;137:579-90 pubmed publisher
    ..The accessibility of ions to one of the chambers in the central pathway likely serves a regulatory function. ..
  6. Qian F, El Hiani Y, Linsdell P. Functional arrangement of the 12th transmembrane region in the CFTR chloride channel pore based on functional investigation of a cysteine-less CFTR variant. Pflugers Arch. 2011;462:559-71 pubmed publisher
    ..We also propose a mechanism by which these seemingly structurally symmetrical TMs make asymmetric contributions to the functional properties of the channel pore. ..
  7. Li M, Demsey A, Qi J, Linsdell P. Cysteine-independent inhibition of the CFTR chloride channel by the cysteine-reactive reagent sodium (2-sulphonatoethyl) methanethiosulphonate. Br J Pharmacol. 2009;157:1065-71 pubmed publisher
    ..Given the very widespread use of MTS reagents in functional studies, our findings offer a broadly applicable caveat to the interpretation of results obtained from such studies. ..
  8. Wilson D, Wilson C, Moldoveanu C, Resmerita A, Corcoran P, Hoang L, et al. Neopentylglycolborylation of aryl mesylates and tosylates catalyzed by Ni-based mixed-ligand systems activated with Zn. J Am Chem Soc. 2010;132:1800-1 pubmed publisher
    ..the neopentylglycolborylation of ortho-, meta-, and para-substituted electron-rich and electron-deficient aryl mesylates and tosylates...
  9. Nichols A, Luetje C. Transmembrane segment 3 of Drosophila melanogaster odorant receptor subunit 85b contributes to ligand-receptor interactions. J Biol Chem. 2010;285:11854-62 pubmed publisher
    ..This finding can serve as a starting point for future detailed analysis of the molecular basis for odorant recognition by insect ORs, a novel class of ligand-gated channel. ..

More Information

Publications62

  1. Bargeton B, Kellenberger S. The contact region between three domains of the extracellular loop of ASIC1a is critical for channel function. J Biol Chem. 2010;285:13816-26 pubmed publisher
    ..4 to 6.8, suggesting that this zone undergoes conformational changes during inactivation. Our study identifies a region in ASIC1a whose integrity is required for normal channel function. ..
  2. Fatehi M, Linsdell P. Novel residues lining the CFTR chloride channel pore identified by functional modification of introduced cysteines. J Membr Biol. 2009;228:151-64 pubmed publisher
    ..We suggest that TM11 contributes to the CFTR pore and that the extracellular loop between TMs 11 and 12 lies close to the outer mouth of the pore. ..
  3. Wang W, El Hiani Y, Linsdell P. Alignment of transmembrane regions in the cystic fibrosis transmembrane conductance regulator chloride channel pore. J Gen Physiol. 2011;138:165-78 pubmed publisher
    ..Such functional information is necessary to understand and interpret the three-dimensional structure of the pore. ..
  4. Khodakhah K, Melishchuk A, Armstrong C. Charge immobilization caused by modification of internal cysteines in squid Na channels. Biophys J. 1998;75:2821-9 pubmed
  5. Chang H, Yeh S, Shieh R. A ring of negative charges in the intracellular vestibule of Kir2.1 channel modulates K+ permeation. Biophys J. 2005;88:243-54 pubmed
    ..Based on an ion-conduction model, we propose that the appearance of the substate in the E224G mutant is due to changes of ion gating in association with variations of ion-ion interaction in the permeation pathway. ..
  6. Kamdar G, Penado K, Rudnick G, Stephan M. Functional role of critical stripe residues in transmembrane span 7 of the serotonin transporter. Effects of Na+, Li+, and methanethiosulfonate reagents. J Biol Chem. 2001;276:4038-45 pubmed
    ..The critical stripe residues on TM7 probably represent a close contact region between TM7 and one or more other TMs in the transporter's three-dimensional structure. ..
  7. Li M, Chang T, Silberberg S, Swartz K. Gating the pore of P2X receptor channels. Nat Neurosci. 2008;11:883-7 pubmed publisher
    ..Our results show that TM2 lines the central ion-conduction pore, TM1 is positioned peripheral to TM2 and the flow of ions is minimized in the closed state by a gate formed by the external region of TM2. ..
  8. Fatehi M, Linsdell P. State-dependent access of anions to the cystic fibrosis transmembrane conductance regulator chloride channel pore. J Biol Chem. 2008;283:6102-9 pubmed publisher
    ..We propose further that this conformational change occurs in advance of channel opening, suggesting that multiple distinct closed pore conformations exist. ..
  9. Crich D, Smith M. 1-Benzenesulfinyl piperidine/trifluoromethanesulfonic anhydride: a potent combination of shelf-stable reagents for the low-temperature conversion of thioglycosides to glycosyl triflates and for the formation of diverse glycosidic linkages. J Am Chem Soc. 2001;123:9015-20 pubmed
    ..The glycosyl triflates are rapidly and cleanly converted to glycosides, upon treatment with alcohols, in good yield and selectivity. ..
  10. Tsunenari T, Sun H, Williams J, Cahill H, Smallwood P, Yau K, et al. Structure-function analysis of the bestrophin family of anion channels. J Biol Chem. 2003;278:41114-25 pubmed
    ..These experiments provide the first structural analysis of the bestrophin channel family. ..
  11. Zomot E, Kanner B. The interaction of the gamma-aminobutyric acid transporter GAT-1 with the neurotransmitter is selectively impaired by sulfhydryl modification of a conformationally sensitive cysteine residue engineered into extracellular loop IV. J Biol Chem. 2003;278:42950-8 pubmed
    ..Moreover, GABA is unable to suppress the transient currents. Our results indicate that part of extracellular loop IV is conformationally sensitive, and its modification selectively abolishes the interaction of the transporter with GABA. ..
  12. Smith S, Liu X, Zhang Z, Sun F, Kriewall T, McCarty N, et al. CFTR: covalent and noncovalent modification suggests a role for fixed charges in anion conduction. J Gen Physiol. 2001;118:407-31 pubmed
    ..The results are consistent with the hypothesis that in wild-type CFTR, R334 occupies a position where its charge can influence the distribution of anions near the mouth of the pore. ..
  13. Bell D, Yao H, Saenger R, Riley J, Siegelbaum S. Changes in local S4 environment provide a voltage-sensing mechanism for mammalian hyperpolarization-activated HCN channels. J Gen Physiol. 2004;123:5-19 pubmed
  14. Kronengold J, Trexler E, Bukauskas F, Bargiello T, Verselis V. Pore-lining residues identified by single channel SCAM studies in Cx46 hemichannels. Cell Commun Adhes. 2003;10:193-9 pubmed
    ..Although all six subunits can be modified by smaller MTS reagents, modifications appear limited to fewer subunits with larger reagents. ..
  15. Ehnes C, Forster I, Kohler K, Bacconi A, Stange G, Biber J, et al. Structure-function relations of the first and fourth predicted extracellular linkers of the type IIa Na+/Pi cotransporter: I. Cysteine scanning mutagenesis. J Gen Physiol. 2004;124:475-88 pubmed
  16. Ehnes C, Forster I, Bacconi A, Kohler K, Biber J, Murer H. Structure-function relations of the first and fourth extracellular linkers of the type IIa Na+/Pi cotransporter: II. Substrate interaction and voltage dependency of two functionally important sites. J Gen Physiol. 2004;124:489-503 pubmed
    ..The simulations predict that cys substitution at Gly-134 or cys modification of Cys-533 alters the preferred orientation of the empty carrier from an inward to outward-facing conformation for hyperpolarizing voltages. ..
  17. Loussouarn G, Phillips L, Masia R, Rose T, Nichols C. Flexibility of the Kir6.2 inward rectifier K(+) channel pore. Proc Natl Acad Sci U S A. 2001;98:4227-32 pubmed
    ..2 model this narrowing excludes all ions. To allow entry of ions as large as MTSPTrEA(+) or qBBr(+), the entrance must widen to >8 A, but this widening is readily accomplished by minimal M2 helix motion and side-chain rearrangement. ..
  18. Lambert G, Forster I, Biber J, Murer H. Cysteine residues and the structure of the rat renal proximal tubular type II sodium phosphate cotransporter (rat NaPi IIa). J Membr Biol. 2000;176:133-41 pubmed
    ..A revised secondary structure is proposed which includes two partially repeated motifs that are connected by disulfide bridges formed between cysteine pairs C306-C334 and C225-C520. ..
  19. Roux M, Martínez Maza R, Le Goff A, Lopez Corcuera B, Aragon C, Supplisson S. The glial and the neuronal glycine transporters differ in their reactivity to sulfhydryl reagents. J Biol Chem. 2001;276:17699-705 pubmed
    ..Together, these results indicate that EL1 conformation differs between GlyT1b and GlyT2a and is modified by substrate binding and translocation. ..
  20. Chaabane H, Vulliet E, Joux F, Lantoine F, Conan P, Cooper J, et al. Photodegradation of sulcotrione in various aquatic environments and toxicity of its photoproducts for some marine micro-organisms. Water Res. 2007;41:1781-9 pubmed
    ..Toxicological studies on two marine heterotrophic bacteria and one cyanobacterium showed absence of effects up to 100 microgL(-1) for both sulcotrione and its photoproducts. ..
  21. Liu X, Alexander C, Serrano J, Borg E, Dawson D. Variable reactivity of an engineered cysteine at position 338 in cystic fibrosis transmembrane conductance regulator reflects different chemical states of the thiol. J Biol Chem. 2006;281:8275-85 pubmed
    ..Metal liganding alters thiol reactivity and may, in some cases, catalyze oxidation of the thiol to an unreactive form such as a sulfinic or sulfonic acid. ..
  22. Zhen X, Xie C, Fitzmaurice A, Schoonover C, Orenstein E, Yang J. Functional architecture of the inner pore of a voltage-gated Ca2+ channel. J Gen Physiol. 2005;126:193-204 pubmed
    ..This work provides an impetus for future studies on ion permeation, gating, and drug binding of VGCCs. ..
  23. Engh A, Maduke M. Cysteine accessibility in ClC-0 supports conservation of the ClC intracellular vestibule. J Gen Physiol. 2005;125:601-17 pubmed
    ..2004). These results support the hypothesis that both secondary and tertiary structures in the intracellular vestibule are conserved among ClC family members, even in regions of very low sequence similarity. ..
  24. Gandhi C, Clark E, Loots E, Pralle A, Isacoff E. The orientation and molecular movement of a k(+) channel voltage-sensing domain. Neuron. 2003;40:515-25 pubmed
    ..We find that the S1-S3 helices have one end that is externally exposed, S3 does not undergo a transmembrane motion, and S4 lies in close apposition to the pore domain in the resting and activated state. ..
  25. Snyder P. Liddle's syndrome mutations disrupt cAMP-mediated translocation of the epithelial Na(+) channel to the cell surface. J Clin Invest. 2000;105:45-53 pubmed
    ..This sequence is the target for mutations that cause Liddle's syndrome, suggesting that cAMP-mediated translocation of ENaC to the cell surface is defective in this genetic form of hypertension. ..
  26. Lin C, Chen T. Probing the pore of ClC-0 by substituted cysteine accessibility method using methane thiosulfonate reagents. J Gen Physiol. 2003;122:147-59 pubmed
    ..Thus, the proposal that the glutamate side chain is the fast gate of the channel is applicable to ClC-0, revealing a structural and functional conservation of ClC channels between bacterial and vertebrate species...
  27. Sunami A, Tracey A, Glaaser I, Lipkind G, Hanck D, Fozzard H. Accessibility of mid-segment domain IV S6 residues of the voltage-gated Na+ channel to methanethiosulfonate reagents. J Physiol. 2004;561:403-13 pubmed
    ..We therefore suggest that the middle of IV-S6 is an alpha-helix, and we propose a model of the open channel, based on MthK, in which Phe-1579 and Val-1583 face the pore. ..
  28. Clyne J, Wang L, Hume R. Mutational analysis of the conserved cysteines of the rat P2X2 purinoceptor. J Neurosci. 2002;22:3873-80 pubmed
    ..We also suggest that C124, C130, C147, and C158 form two disulfide bonds, but we are unable to assign specific cysteine pairs to these two bonds. ..
  29. Subbiah R, Clarke C, Smith D, Zhao J, Campbell T, Vandenberg J. Molecular basis of slow activation of the human ether-a-go-go related gene potassium channel. J Physiol. 2004;558:417-31 pubmed
    ..The main conclusions we can draw from these data are that in WT channels K525 stabilizes the closed state, R531 stabilizes the open state and R534 participates in interactions that stabilize pre-open closed states. ..
  30. Liu X, Smith S, Sun F, Dawson D. CFTR: covalent modification of cysteine-substituted channels expressed in Xenopus oocytes shows that activation is due to the opening of channels resident in the plasma membrane. J Gen Physiol. 2001;118:433-46 pubmed
    ..These findings demonstrate that in Xenopus oocytes, the major mechanism of CFTR activation by cAMP is by means of an increase in the open probability of CFTR channels. ..
  31. del Camino D, Holmgren M, Liu Y, Yellen G. Blocker protection in the pore of a voltage-gated K+ channel and its structural implications. Nature. 2000;403:321-5 pubmed
    ..This bend would occur at a Pro-X-Pro sequence that is highly conserved in Kv channels, near the site of activation gating. ..
  32. Nakajo K, Kubo Y. KCNE1 and KCNE3 stabilize and/or slow voltage sensing S4 segment of KCNQ1 channel. J Gen Physiol. 2007;130:269-81 pubmed
    ..These results offer new insight into the mechanism of KCNQ1 channel modulation by KCNE1 and KCNE3. ..
  33. Xiao J, Zhen X, Yang J. Localization of PIP2 activation gate in inward rectifier K+ channels. Nat Neurosci. 2003;6:811-8 pubmed
    ..These results suggest that the TM2 helices undergo conformation changes upon PIP2 binding/unbinding, but neither they nor the cytoplasmic pore close fully to form a physical gate for K+ conduction. ..
  34. Kaplan R, Mayor J, Brauer D, Kotaria R, Walters D, Dean A. The yeast mitochondrial citrate transport protein. Probing the secondary structure of transmembrane domain iv and identification of residues that likely comprise a portion of the citrate translocation pathway. J Biol Chem. 2000;275:12009-16 pubmed
    ..We infer that the water-accessible face comprises a portion of the substrate translocation pathway through the CTP, whereas the water-inaccessible surface faces the lipid bilayer. ..
  35. Fors B, Watson D, Biscoe M, Buchwald S. A highly active catalyst for Pd-catalyzed amination reactions: cross-coupling reactions using aryl mesylates and the highly selective monoarylation of primary amines using aryl chlorides. J Am Chem Soc. 2008;130:13552-4 pubmed publisher
    ..This catalyst system enables the use of aryl mesylates as a coupling partner in C-N bond-forming reactions...
  36. Cui Y, Wang W, Fan Z. Cytoplasmic vestibule of the weak inward rectifier Kir6.2 potassium channel. J Biol Chem. 2002;277:10523-30 pubmed
    ..Data are consistent with the hypothesis that residues Ile-210-Ser-212 line a funnel-shaped vestibule of 20-25 A in diameter, which remains unchanged during channel gating. ..
  37. Xie C, Zhen X, Yang J. Localization of the activation gate of a voltage-gated Ca2+ channel. J Gen Physiol. 2005;126:205-12 pubmed
    ..Our results suggest that the S6 helices of the alpha1 subunit of VGCCs undergo conformation changes during gating and the activation gate is located at the intracellular end of the pore. ..
  38. Simoes M, Garneau L, Klein H, Banderali U, Hobeila F, Roux B, et al. Cysteine mutagenesis and computer modeling of the S6 region of an intermediate conductance IKCa channel. J Gen Physiol. 2002;120:99-116 pubmed
    ..According to this model, closure by the gate should occur at a point located between the T278 and V282 residues. ..
  39. Phillips L, Enkvetchakul D, Nichols C. Gating dependence of inner pore access in inward rectifier K(+) channels. Neuron. 2003;37:953-62 pubmed
  40. Lerche H, Peter W, Fleischhauer R, Pika Hartlaub U, Malina T, Mitrovic N, et al. Role in fast inactivation of the IV/S4-S5 loop of the human muscle Na+ channel probed by cysteine mutagenesis. J Physiol. 1997;505 ( Pt 2):345-52 pubmed
  41. Bonnet J, Bonnemoy F, Dusser M, Bohatier J. Toxicity assessment of the herbicides sulcotrione and mesotrione toward two reference environmental microorganisms: Tetrahymena pyriformis and Vibrio fischeri. Arch Environ Contam Toxicol. 2008;55:576-83 pubmed publisher
  42. Zhang Z, Song B, McCarty N. State-dependent chemical reactivity of an engineered cysteine reveals conformational changes in the outer vestibule of the cystic fibrosis transmembrane conductance regulator. J Biol Chem. 2005;280:41997-2003 pubmed
  43. Sesti F, Rajan S, Gonzalez Colaso R, Nikolaeva N, Goldstein S. Hyperpolarization moves S4 sensors inward to open MVP, a methanococcal voltage-gated potassium channel. Nat Neurosci. 2003;6:353-61 pubmed publisher
    ..Thus, MVP opens with sensors inward indicating a reversal of S4 position and pore state compared to classical channels. Homologous channels in mammals and plants are expected to function similarly...
  44. Ni Y, Chen J, Androutsellis Theotokis A, Huang C, Moczydlowski E, Rudnick G. A lithium-induced conformational change in serotonin transporter alters cocaine binding, ion conductance, and reactivity of Cys-109. J Biol Chem. 2001;276:30942-7 pubmed
    ..These results are consistent with Li(+) inducing a conformational change that exposes Cys-109, decreases cocaine affinity, and increases the uncoupled inward current. ..
  45. Chahine M, Deschenes I, Trottier E, Chen L, Kallen R. Restoration of fast inactivation in an inactivation-defective human heart sodium channel by the cysteine modifying reagent benzyl-MTS: analysis of IFM-ICM mutation. Biochem Biophys Res Commun. 1997;233:606-10 pubmed
  46. Sucic S, Bryan Lluka L. Roles of transmembrane domain 2 and the first intracellular loop in human noradrenaline transporter function: pharmacological and SCAM analysis. J Neurochem. 2005;94:1620-30 pubmed
    ..The results suggest that this region of hNET is important for interactions with antidepressants and cocaine, but it is probably not involved in substrate translocation mechanisms. ..
  47. Zhou Y, Kanner B. Transporter-associated currents in the gamma-aminobutyric acid transporter GAT-1 are conditionally impaired by mutations of a conserved glycine residue. J Biol Chem. 2005;280:20316-24 pubmed
    ..Our results can be explained by a model invoking two outward-facing states of the empty transporter and a defective transition between these states in the glycine 80 mutants. ..
  48. Latorre R, Olcese R, Basso C, Gonzalez C, Munoz F, Cosmelli D, et al. Molecular coupling between voltage sensor and pore opening in the Arabidopsis inward rectifier K+ channel KAT1. J Gen Physiol. 2003;122:459-69 pubmed
    ..The results demonstrate that the putative voltage-sensing charges of S4 move inward when the KAT1 channels open. ..
  49. Kronengold J, Trexler E, Bukauskas F, Bargiello T, Verselis V. Single-channel SCAM identifies pore-lining residues in the first extracellular loop and first transmembrane domains of Cx46 hemichannels. J Gen Physiol. 2003;122:389-405 pubmed
    ..If representative of open channels and hemichannels, these data indicate E1 as constituting a significant portion of this inner, pore-forming wall, and TM1 contributing as pore-lining in the extracellular portion of transmembrane span. ..
  50. Yamamoto H, Sasaki I, Hirai Y, Namba K, Imagawa H, Nishizawa M. Silaphenylmercuric triflate catalyzed reactions: synthesis of a solid-supported mercuric salt catalyst. Angew Chem Int Ed Engl. 2009;48:1244-7 pubmed publisher
    ..An efficient flow reaction system for indole synthesis and arylyne cyclization is also described (see figure). ..
  51. Cai Y, Li J, Chen W, Xie M, Liu X, Lin L, et al. Catalytic asymmetric sulfenylation of unprotected 3-substituted oxindoles. Org Lett. 2012;14:2726-9 pubmed publisher
    ..Utilizing readily available N-(phenylthio)phthalimide as the sulfur source, a wide range of optically active 3-phenylthiooxindoles were obtained in excellent yields with excellent enantioselectivities under mild reaction conditions...
  52. Eom D, Park S, Park Y, Ryu T, Lee P. Synthesis of indenes via Brønsted acid catalyzed cyclization of diaryl- and alkyl aryl-1,3-dienes. Org Lett. 2012;14:5392-5 pubmed publisher
    ..In this approach, treatment of symmetric or unsymmetric diaryl- and alkyl aryl-1,3-dienes with a catalytic amount of trifluoromethanesulfonic acid gives a variety of indene derivatives in good to excellent yields under mild conditions. ..
  53. Li X, Wang H, Yang S. Sc(OTf)3-catalyzed dehydrogenative cyclization for synthesis of N-methylacridones. Org Lett. 2013;15:1794-7 pubmed publisher
    ..Furthermore, the procedure involved is both environmental friendly and atom efficient; H2O is the only byproduct in this reaction. ..