@article {2205, title = {Template-assembled synthetic G-quartets (TASQs)}, journal = {Angewandte Chemie-International Edition}, volume = {47}, number = {26}, year = {2008}, note = {ISI Document Delivery No.: 317SSTimes Cited: 8Cited Reference Count: 38Nikan, Mehran Sherman, John C.}, pages = {4900-4902}, type = {Article}, keywords = {cation, CAVITANDS, CHEMISTRY, DEOXYGUANOSINE, DERIVATIVES, G-quartets, GUANOSINE, HOST-GUEST COMPLEXATION, NUCLEOSIDES, NUCLEOTIDE, ORGANIC-SOLVENTS, QUADRUPLEX STRUCTURE, supramolecular, supramolecular chemistry, SYNTHESIS, TELOMERIC DNA OLIGONUCLEOTIDES, TEMPLATE}, isbn = {1433-7851}, url = {://000257040800022}, author = {Nikan, M. and Sherman, J. C.} } @article {736, title = {Molecules that can{\textquoteright}t resist templation}, journal = {Chemical Communications}, number = {14}, year = {2003}, note = {ISI Document Delivery No.: 696EETimes Cited: 26Cited Reference Count: 47}, pages = {1617-1623}, type = {Article}, abstract = {The encapsulation of molecules or ions has captured the interest of a variety of researches, including those using zeolites, fullerenes, micelles, clathrates, and metal coordination complexes. Multiple hemispherical units have been used to create organic cages that can bind guests reversibly or irreversibly. Often such cages will only form in the presence of a guest, which acts as a template. This article summarizes some of the work in this field.}, keywords = {CAPSULES, CARCEPLEXES, CAVITANDS, CONTAINER COMPOUNDS, CRYSTAL-STRUCTURE, HEMICARCEPLEXES, HOST-GUEST COMPLEXATION, PHASE, REVERSIBLE ENCAPSULATION, SHELL CLOSURE}, isbn = {1359-7345}, url = {://000183872700002}, author = {Sherman, J.} } @article {678, title = {Template effect where 1-3 molecules drive formation of a trimer carceplex}, journal = {Chemistry-a European Journal}, volume = {9}, number = {14}, year = {2003}, note = {ISI Document Delivery No.: 706XATimes Cited: 6Cited Reference Count: 46}, month = {Jul}, pages = {3253-3262}, type = {Article}, abstract = {The template effect in the formation of a trimer carceplex using 1-3 molecules as templates is explored. Thirteen different templates were studied and template ratios were measured for templates of like and unlike molecularity. Five transition-state models were studied for their binding abilities to see if these mirror the template ratios. The chemical shifts of the guests and the thermodynamic and kinetic values for templation suggest that binding is key, often tight, and that the guest determining step is formation of the last covalent bond. The molecular dynamics of guests as well as the conformational dynamics of both hosts and guests further addresses nature of the recognition between host and guest. Finally, we were surprised to discover that water can bind reversibly to the trimer carceplexes, which will have ramifications to any inner phase reactions conducted inside the cage.}, keywords = {AMPLIFICATION, BARRIER, BINDING, CAPTURE, carceplex, CHEMISTRY, DIELS-ALDER REACTION, DYNAMICS, ELUCIDATION, ENCAPSULATION, HOST-GUEST COMPLEXATION, host-guest systems, molecular recognition, RESORCINARENE CAPSULE, REVERSIBLE, supramolecular, TEMPLATE SYNTHESIS}, isbn = {0947-6539}, url = {://000184479300009}, author = {Makeiff, D. A. and Sherman, J. C.} } @article {4577, title = {Carceplexes and hemicarceplexes}, journal = {Chemical Reviews}, volume = {99}, number = {4}, year = {1999}, note = {ISI Document Delivery No.: 189WZTimes Cited: 258Cited Reference Count: 229}, month = {Apr}, pages = {931-967}, type = {Review}, keywords = {CONSTRICTIVE BINDING, CRYSTAL-STRUCTURE, DIELS-ALDER REACTION, ENDOHEDRAL METALLOFULLERENES, ENERGY-TRANSFER, HOST-GUEST COMPLEXATION, HYDROGEN-BONDING PREFERENCES, REVERSIBLE MOLECULAR CAPSULES, SELF-ASSEMBLED MONOLAYERS, supramolecular chemistry, TRIPLET}, isbn = {0009-2665}, url = {://000079930300001}, author = {Jasat, A. and Sherman, J. C.} } @article {4503, title = {Elucidation of "twistomers" in container compounds}, journal = {Journal of the American Chemical Society}, volume = {121}, number = {9}, year = {1999}, note = {ISI Document Delivery No.: 176GRTimes Cited: 28Cited Reference Count: 18}, month = {Mar}, pages = {1962-1963}, type = {Article}, keywords = {CARCEPLEXES, CRYSTAL-STRUCTURE, HOST-GUEST COMPLEXATION, LANTHANIDE SHIFT-REAGENTS}, isbn = {0002-7863}, url = {://000079143700029}, author = {Chapman, R. G. and Sherman, J. C.} } @article {4224, title = {Reversible molecular capsules composed of two cavitands linked via an assortment of charged-hydrogen bonds and covalent bonds}, journal = {Journal of the American Chemical Society}, volume = {120}, number = {38}, year = {1998}, note = {ISI Document Delivery No.: 125EVTimes Cited: 42Cited Reference Count: 29}, month = {Sep}, pages = {9818-9826}, type = {Article}, abstract = {Six new cavitand bowls are reported (6, 7, 8, 9, 11, and 12), as are three bis-bowl compounds (4, 13, and 14). Eight new complexes (4.guest, 7C.guest, 8C.guest, 9C.guest, 14.guest, 15.guest, 15C.guest, and 16C.guest) that reversibly encapsulate small molecules are reported. Two or more charged-hydrogen bonds (CHBs) or covalent linkages between the bowls are required to form stable complexes. Guest exchange rates vary from milliseconds to days. Thermodynamically, these complexes display an enthalpy-entropy compensation. The relative stability of complex 3.pyrazine versus complex 3.chloroform is 170000 in nitrobenzene-d(5) at 298 It. Apparent stability constants in nitrobenzene-d(5) at 298 K yield 1.1 x 10(9) M-1 for complex 3.pyrazine. The absolute stability constant for complex 4.pyrazine in nitrobenzene-d(5) at 333 K is 3.5 x 10(6) M-1.}, keywords = {BINDING, carceplex, CHEMISTRY, ENCAPSULATION, HEMICARCERANDS, HOST-GUEST COMPLEXATION, ORGANIC-MOLECULES, RELEASE, TEMPLATION}, isbn = {0002-7863}, url = {://000076225200012}, author = {Chapman, R. G. and Sherman, J. C.} } @article {4351, title = {Water-soluble cavitands: Synthesis of methylene-bridged resorcin[4]arenes containing hydroxyls and phosphates at their feet and bromomethyls and thiomethyls at their rims}, journal = {Journal of Organic Chemistry}, volume = {63}, number = {20}, year = {1998}, note = {ISI Document Delivery No.: 127ZGTimes Cited: 11Cited Reference Count: 31}, month = {Oct}, pages = {6824-6829}, type = {Article}, abstract = {The synthesis of rim-functionalized methylene-bridged resorcin[4]arenes ("cavitands") containing hydrophilic propanol or water-solublilizing propylphosphate feet is described. The cavitands possess the synthetically useful benzylthiol (cavitands 6 and 16) or benzylbromide (cavitands 9 and 11) functionalities at their rims, which are suitable for further derivatization near the hydrophobic cavity of the cavitand. These water-soluble cavitands represent new building blocks that are ideal for use in aqueous supramolecular chemistry. As an example of their synthetic utility in supramolecular studies, we have reacted phosphate-footed cavitands 11 and 16 with cysteine-containing peptide 17 and chloroacetylated peptide 19, respectively, to afford the corresponding de novo proteins 18 and 20.}, keywords = {ADSORPTION, BUILDING-BLOCKS, CARCERANDS, ENCAPSULATION, HOST-GUEST COMPLEXATION, MOLECULAR, PHASE, RECOGNITION, RESORCINARENES, SELF-ASSEMBLED MONOLAYERS}, isbn = {0022-3263}, url = {://000076380300019}, author = {Mezo, A. R. and Sherman, J. C.} } @article {3322, title = {AN ASYMMETRIC CARCEPLEX AND NEW CRYSTAL-STRUCTURE YIELD INFORMATION REGARDING A 1-MILLION-FOLD TEMPLATE EFFECT}, journal = {Journal of Organic Chemistry}, volume = {60}, number = {5}, year = {1995}, note = {ISI Document Delivery No.: QL605Times Cited: 48Cited Reference Count: 50}, month = {Mar}, pages = {1207-1213}, type = {Article}, abstract = {We report the incorporation of methyl {\textquoteright}{\textquoteright}feet{\textquoteright}{\textquoteright} as pendant groups in cavitands and carceplexes and their use in the creation of an asymmetric carceplex and the facilitation of the determination of the crystal structure of a carceplex. From the asymmetric carceplex, we have determined a 19 kcal/mol energy barrier to rotation of the guest pyrazine about the host{\textquoteright}s pseudo-C-2 axes, which demonstrates a high degree of complementarity between the shell of the carceplex and the guest pyrazine. The crystal structure reveals the extensive conjugation of the aryl ethers into the aromatic rings of the host when pyrazine is the guest. This result helps explain why pyrazine is, to date, the best template for the reaction to form the carceplex and thus provides insight to the powerful template effect that is the hallmark of this carceplex reaction. Thus, the investigation of this template effect provides a sensitive probe into noncovalent interactions in general and may be useful in the understanding of recognition in both natural systems such as enzyme/substrate complexes and in non-natural systems such as designed self-assembling structures.}, keywords = {4 PORTALS, CAPTURE, CAVITANDS, CONSTRICTIVE BINDING, DERIVATIVES, HEMICARCERAND, HOST-GUEST COMPLEXATION, RELEASE}, isbn = {0022-3263}, url = {://A1995QL60500025}, author = {Fraser, J. R. and Borecka, B. and Trotter, J. and Sherman, J. C.} } @article {3322, title = {AN ASYMMETRIC CARCEPLEX AND NEW CRYSTAL-STRUCTURE YIELD INFORMATION REGARDING A 1-MILLION-FOLD TEMPLATE EFFECT}, journal = {Journal of Organic Chemistry}, volume = {60}, number = {5}, year = {1995}, note = {ISI Document Delivery No.: QL605Times Cited: 48Cited Reference Count: 50}, month = {Mar}, pages = {1207-1213}, type = {Article}, abstract = {We report the incorporation of methyl {\textquoteright}{\textquoteright}feet{\textquoteright}{\textquoteright} as pendant groups in cavitands and carceplexes and their use in the creation of an asymmetric carceplex and the facilitation of the determination of the crystal structure of a carceplex. From the asymmetric carceplex, we have determined a 19 kcal/mol energy barrier to rotation of the guest pyrazine about the host{\textquoteright}s pseudo-C-2 axes, which demonstrates a high degree of complementarity between the shell of the carceplex and the guest pyrazine. The crystal structure reveals the extensive conjugation of the aryl ethers into the aromatic rings of the host when pyrazine is the guest. This result helps explain why pyrazine is, to date, the best template for the reaction to form the carceplex and thus provides insight to the powerful template effect that is the hallmark of this carceplex reaction. Thus, the investigation of this template effect provides a sensitive probe into noncovalent interactions in general and may be useful in the understanding of recognition in both natural systems such as enzyme/substrate complexes and in non-natural systems such as designed self-assembling structures.}, keywords = {4 PORTALS, CAPTURE, CAVITANDS, CONSTRICTIVE BINDING, DERIVATIVES, HEMICARCERAND, HOST-GUEST COMPLEXATION, RELEASE}, isbn = {0022-3263}, url = {://A1995QL60500025}, author = {Fraser, J. R. and Borecka, B. and Trotter, J. and Sherman, J. C.} } @article {3520, title = {CARCEPLEXES AND HEMICARCEPLEXES - MOLECULAR ENCAPSULATION - FROM HOURS TO FOREVER}, journal = {Tetrahedron}, volume = {51}, number = {12}, year = {1995}, note = {ISI Document Delivery No.: QN982Times Cited: 70Cited Reference Count: 124}, month = {Mar}, pages = {3395-3422}, type = {Review}, keywords = {4, CARBON NANOTUBES, CARCERANDS, CAVITANDS, CHEMISTRY, CONSTRICTIVE BINDING, CONTAINER COMPOUNDS, HEMICARCERANDS, HOST-GUEST COMPLEXATION, PORTALS, SHELL CLOSURE, supramolecular}, isbn = {0040-4020}, url = {://A1995QN98200001}, author = {Sherman, J. C.} } @article {3278, title = {TEMPLATION EFFECTS ON FORMATION OF A HEMICARCEPLEX}, journal = {Supramolecular Chemistry}, volume = {5}, number = {1}, year = {1995}, note = {ISI Document Delivery No.: RX096Times Cited: 15Cited Reference Count: 36}, pages = {31-37}, type = {Article}, abstract = {We have shown previously that the reaction to form carceplex 3 . guest has dramatic templation requirements where the best template molecule studied is one million times more effective at bridging the two bowl-shaped precursors than the poorest template. Here, we investigate the template requirements for the formation of hemicarceplex 4 . guest which is similar to carceplex 3 . guest in cavity size and shape. The two compounds differ in that 4 . guest lacks one of the four inter-bowl methylene bridges and thus has a portal and reduced symmetry relative to carceplex 3 . guest (C-2v vs D-4h). Thus, the template requirements for hemicarceplex 4 . guest are more stringent because the two howls can, in principle, misalign. We have found that despite these differences, the same template effect holds. We conclude that the same forces are at play in each reaction. These forces include 1) favorable van der Waals interactions between the template molecule and the forming cavity of the carceplex or hemicarceplex 2) unfavorable steric strain being imparted to the complex and 3) hydrogen bonds between the bowls. We also demonstrate the utility of matrix-assisted laser desorption ionization (MALDI) as a mild mass spectrometric technique for non-volatile organic compounds and complexes.}, keywords = {4 PORTALS, BINDING, CAPTURE, CARCERANDS, CONSTRICTIVE, HOST-GUEST COMPLEXATION, LASER DESORPTION IONIZATION, MASS-SPECTROMETRY, POLYMERS, RECOGNITION, RELEASE}, isbn = {1061-0278}, url = {://A1995RX09600007}, author = {Chopra, N. and Sherman, J. C.} } @article {3060, title = {DESIGN AND SYNTHESIS OF ANALOGS OF IONOMYCIN}, journal = {Canadian Journal of Chemistry-Revue Canadienne De Chimie}, volume = {72}, number = {6}, year = {1994}, note = {ISI Document Delivery No.: NV309Times Cited: 7Cited Reference Count: 34}, month = {Jun}, pages = {1500-1511}, type = {Article}, abstract = {Based on the analysis of the crystal structure of the Ca2+ salt of ionomycin and the chemical and physical data on ionomycin, a number of ionomycin analogues have been synthesized to study the structural features affecting the Ca2+ binding and transport. Compounds 2, 3, and 4 were synthesized to study the effect of additional intramolecular oxygen coordination sites on Ca2+ transport. Compounds 5a-5d were prepared to study the effect of lipid solubility on Ca2+ binding and transport. Compounds 6a-6c were prepared to study the effect of the distance between the P-diketone and the carboxyl group on Ca2+ transport. A general synthetic route to these compounds has been developed. The key reactions in this route are the consecutive regioselective alkylations of the dianion of 2,4-pentanedione with the appropriate bromides.}, keywords = {ACID, HOST-GUEST COMPLEXATION, IONOPHORE, RESOLUTION}, isbn = {0008-4042}, url = {://A1994NV30900010}, author = {Hu, Thomas Q. and Weiler, L.} }