@article {2182, title = {Synthesis, characterisation, and in vitro evaluation of Pro(2)-Ile(3)-S-deoxo-amaninamide and Pro(2)-D-allo-Ile(3)-S-deoxo-amaninamide: Implications for structure-activity relationships in amanitin conformation and toxicity}, journal = {Chemistry-a European Journal}, volume = {14}, number = {11}, year = {2008}, note = {ISI Document Delivery No.: 291XITimes Cited: 0Cited Reference Count: 39May, Jonathan P. Fournier, Pierre Patrick, Brian O. Perrin, David M.}, pages = {3410-3417}, type = {Article}, abstract = {The amatoxins are a family of toxic bicyclic peptides that inhibit RNA polymerase II. Herein we discuss an improved synthesis of these compounds from easily obtainable amino acids by means of a solid-phase methodology. Interestingly, we obtained two products of the same mass following our final macrocyclisation, relating to a similar distribution of products described in some previous reports. One of these products was the desired amatoxin; Pro(2)-Ile(3)-S-deoxo-amaninamide 1b. The other compound, after thorough investigation, was confirmed to be the epimer Pro(2)-D-allo-Ile(3)-S-deoxo-amaninamide la, not an atropisomer structure as previously suggested in syntheses of related amanitin analogues. Crystallographic data of la confirms the presence of a beta II-turn, rather than a PI-turn common to the natural toxin and 1b. This difference explains the large variation in CD spectra, although it seems to have relatively little effect on the bioactivity in vitro. These data provide new insights into the bicyclic amatoxin structure.}, keywords = {ALPHA-AMANITIN, amatoxin, atropisomerism, circular dichroism, CRYSTALLINE STATE, CYCLIZATION, CYSTEINE SULFHYDRYL-GROUPS, EPIMERIZATION, MOLECULAR-STRUCTURE, PEPTIDES, RESOLUTION, RNA-POLYMERASE-II, SERIES, TOXIN BETA-AMANITIN, transcription}, isbn = {0947-6539}, url = {://000255230200020}, author = {May, J. P. and Fournier, P. and Patrick, B. O. and Perrin,David M.} } @article {1359, title = {Structure-reactivity correlations for solid-state enantioselective photochemical reactions established directly from powder X-ray diffraction}, journal = {Journal of the American Chemical Society}, volume = {128}, number = {49}, year = {2006}, note = {ISI Document Delivery No.: 113CMTimes Cited: 5Cited Reference Count: 29Cheung, Eugene Y. Harris, Kenneth D. M. Kang, Ting Scheffer, John R. Trotter, James}, month = {Dec}, pages = {15554-15555}, type = {Article}, keywords = {ASYMMETRIC INDUCTION, CHEMISTRY, CRYSTALLINE STATE, GENETIC ALGORITHM, ORGANIC-PHOTOCHEMISTRY, SALTS}, isbn = {0002-7863}, url = {://000242575300003}, author = {Cheung, E. Y. and Harris, K. D. M. and Kang, T. and Scheffer, J. R. and Trotter, J.} } @article {1359, title = {Structure-reactivity correlations for solid-state enantioselective photochemical reactions established directly from powder X-ray diffraction}, journal = {Journal of the American Chemical Society}, volume = {128}, number = {49}, year = {2006}, note = {ISI Document Delivery No.: 113CMTimes Cited: 5Cited Reference Count: 29Cheung, Eugene Y. Harris, Kenneth D. M. Kang, Ting Scheffer, John R. Trotter, James}, month = {Dec}, pages = {15554-15555}, type = {Article}, keywords = {ASYMMETRIC INDUCTION, CHEMISTRY, CRYSTALLINE STATE, GENETIC ALGORITHM, ORGANIC-PHOTOCHEMISTRY, SALTS}, isbn = {0002-7863}, url = {://000242575300003}, author = {Cheung, E. Y. and Harris, K. D. M. and Kang, T. and Scheffer, J. R. and Trotter, J.} } @inbook {1243, title = {Asymmetric induction in organic photochemistry via the solid-state ionic chiral auxiliary approach}, booktitle = {Organic Solid State Reactions}, series = {Topics in Current Chemistry}, volume = {254}, year = {2005}, note = {ISI Document Delivery No.: BCP68Times Cited: 29Cited Reference Count: 57ReviewHEIDELBERGER PLATZ 3, D-14197 BERLIN, GERMANY}, pages = {233-262}, publisher = {Springer-Verlag Berlin}, organization = {Springer-Verlag Berlin}, address = {Berlin}, abstract = {After a brief introduction and summary of various methods of asymmetric induction in organic photochemistry, the main part of the review covers the solid-state ionic chiral auxiliary approach to asymmetric photochemical synthesis. Application of this technique to the Norrish type II reaction, as well as to the di-Ti-methane and oxa-di-pi-methane photorearrangements, and the Cis, trans-photoisomerization of diarylcyclopropane derivatives is presented and discussed.}, keywords = {ABSOLUTE-CONFIGURATION, ACHIRAL, AMMONIUM CARBOXYLATE SALTS, ASYMMETRIC INDUCTION, auxiliaries, crystal structure-reactivity correlations, CRYSTALLINE STATE, di-pi-methane, ionic chiral, MODIFIED ZEOLITES, MOLECULES, organic photochemistry, PHOTOCYCLIZATION, SINGLE-CRYSTALS, solid state, STRUCTURE-REACTIVITY RELATIONSHIPS, TROPOLONE ETHER}, isbn = {0340-1022}, url = {://000230596800007}, author = {Scheffer, J. R. and Xia, W. J.} } @article {459, title = {Control of enantioselectivity in the photochemical conversion of alpha-oxoamides into beta-lactam derivatives}, journal = {Organic Letters}, volume = {4}, number = {9}, year = {2002}, note = {ISI Document Delivery No.: 545XYTimes Cited: 19Cited Reference Count: 34}, month = {May}, pages = {1443-1446}, type = {Article}, abstract = {[GRAPHIC] Several approaches to asymmetric induction in the alpha-oxoamide (1) to beta-lactam (2) photorearrangement are described. Best results are obtained via irradiation of ionic and covalent chiral auxiliary-containing reactants in the crystalline state and in the interior supercages of zeolites.}, keywords = {AMINO-ACID, ASYMMETRIC INDUCTION, CATION-PI INTERACTIONS, CRYSTALLINE STATE, GAS-PHASE, GEOMETRIC REQUIREMENTS, II, PHOTOCYCLIZATION, REACTIONS, SOLID-STATE PHOTOCHEMISTRY, ZWITTERIONS}, isbn = {1523-7060}, url = {://000175243900009}, author = {Natarajan, A. and Wang, K. and Ramamurthy, V. and Scheffer, J. R. and Patrick, B.} } @article {5187, title = {Enantioselective photochemical synthesis of a beta-lactam via the solid state ionic chiral auxiliary method}, journal = {Synthesis-Stuttgart}, number = {8}, year = {2001}, note = {ISI Document Delivery No.: 448GETimes Cited: 12Cited Reference Count: 20Sp. Iss. SI}, pages = {1253-1257}, type = {Article}, abstract = {Photolysis of crystals of a carboxylic acid-containing N,N-dialkylarylglyoxylamide to which an optically pure ammonium ion (the ionic chiral auxiliary) has been attached through a salt bridge leads to a 91\% isolated yield of a beta -lactam in greater than 99\% enantiomeric excess. Suspension of the crystals in hexane allows the photoreaction to be carried out on a 500 mg scale, thus demonstrating the synthetic utility of the solid stare ionic chiral auxiliary approach to asymmetric synthesis.}, keywords = {ACHIRAL OXO AMIDE, ACID, asymmetric synthesis, beta-lactam, chiral auxiliaries, CRYSTALLINE STATE, HOST, INCLUSION COMPLEXES, PHOTOCHEMISTRY, PHOTOCYCLIZATION, solid state}, isbn = {0039-7881}, url = {://000169617900022}, author = {Scheffer, J. R. and Wang, K. Y.} } @article {4765, title = {Asymmetric induction through the use of remote covalent and ionic chiral auxiliaries in the solid state photochemistry of 2-benzoyladamantane-2-carboxylic acid derivatives}, journal = {Tetrahedron Letters}, volume = {41}, number = {49}, year = {2000}, note = {ISI Document Delivery No.: 379TXTimes Cited: 8Cited Reference Count: 13}, month = {Dec}, pages = {9673-9677}, type = {Article}, abstract = {Attachment of chiral auxiliaries to 2-benzoyladamantane-2-carboxylic acid, either covalently through ester formation with optically pure alcohols, or ionically via salt formation with optically pure amines, leads to substrates whose irradiation in the crystalline state affords chiral rearranged photoproducts in greater than or equal to 96\% diastereo- and enantiomeric excess. (C) 2000 Elsevier Science Ltd. All rights reserved.}, keywords = {CRYSTALLINE STATE, YANG PHOTOCYCLIZATION REACTION}, isbn = {0040-4039}, url = {://000165659500062}, author = {Cheung, E. and Netherton, M. R. and Scheffer, J. R. and Trotter, J. and Zenova, A.} } @article {4765, title = {Asymmetric induction through the use of remote covalent and ionic chiral auxiliaries in the solid state photochemistry of 2-benzoyladamantane-2-carboxylic acid derivatives}, journal = {Tetrahedron Letters}, volume = {41}, number = {49}, year = {2000}, note = {ISI Document Delivery No.: 379TXTimes Cited: 8Cited Reference Count: 13}, month = {Dec}, pages = {9673-9677}, type = {Article}, abstract = {Attachment of chiral auxiliaries to 2-benzoyladamantane-2-carboxylic acid, either covalently through ester formation with optically pure alcohols, or ionically via salt formation with optically pure amines, leads to substrates whose irradiation in the crystalline state affords chiral rearranged photoproducts in greater than or equal to 96\% diastereo- and enantiomeric excess. (C) 2000 Elsevier Science Ltd. All rights reserved.}, keywords = {CRYSTALLINE STATE, YANG PHOTOCYCLIZATION REACTION}, isbn = {0040-4039}, url = {://000165659500062}, author = {Cheung, E. and Netherton, M. R. and Scheffer, J. R. and Trotter, J. and Zenova, A.} }