@article {950,
	title = {Identification and mechanism of a bacterial hydrolyzing UDP-N-acetylglucosamine 2-epimerase},
	journal = {Biochemistry},
	volume = {43},
	number = {44},
	year = {2004},
	note = {ISI Document Delivery No.: 868UVTimes Cited: 13Cited Reference Count: 38},
	month = {Nov},
	pages = {14290-14298},
	type = {Article},
	abstract = {This paper reports the first identification of a fully functional hydrolyzing UDP-N-acetylglucosamine 2-epimerase from a bacterial source. The epimerase (known as SiaA or NeuC from Neisseria meningitidis MC58 group B is shown to catalyze the conversion of UDP-GlcNAc into ManNAc and UDP in the first step of sialic acid (N-acetylneuraminic acid) biosynthesis. The mechanism is proposed to involve an anti elimination of UDP to form 2-acetamidoglucal as an intermediate, followed by the syn addition of water. The observation that the alpha-anomer of ManNAc is the true product and that solvent deuterium is incorporated at C-2 is consistent with this mechanism. The use of the O-18-labeled substrate confirms that the overall hydrolysis reaction proceeds via cleavage of the C-O bond. Furthermore, the putative intermediate 2-acetamidoglucal is shown to serve as a catalytically competent substrate and is enzymatically hydrated to give ManNAc exclusively. Isotope effect studies show that cleavage of the C-H bond is not rate limiting during catalysis. Mutagenesis studies show that three active site carboxylate residues are crucial for catalysis. In two of the mutants that were studied (E122Q and D131N), 2-acetamidoglucal was released from the active site during catalysis, providing direct evidence that the enzyme is capable of catalyzing the anti elimination of UDP from UDP-GlcNAc.},
	keywords = {2-EPIMERASE/N-ACETYLMANNOSAMINE, biosynthesis, CELL-INTERACTIONS, ENZYME, ESCHERICHIA-COLI K1, KINASE, POLYSIALIC ACID, PURIFICATION, RAT-LIVER, SIALIC-ACID, STEREOCHEMISTRY},
	isbn = {0006-2960},
	url = {<Go to ISI>://000224939400045},
	author = {Murkin, A. S. and Chou, W. K. and Wakarchuk, W. W. and Tanner, M. E.}
}
@article {935,
	title = {Stereochemical assignment in acyclic lipids across long distance by circular dichroism: Absolute stereochemistry of the aglycone of caminoside A},
	journal = {Angewandte Chemie-International Edition},
	volume = {43},
	number = {44},
	year = {2004},
	note = {ISI Document Delivery No.: 874FTTimes Cited: 14Cited Reference Count: 30},
	pages = {5946-5951},
	type = {Article},
	keywords = {AGENT, ANTIVIRAL ANTIBIOTICS, B-1, CHROMOPHORES, circular dichroism, CONFIGURATION ANALYSIS, CYCLOVIRACIN, glycolipids, LIPOSOMES, MOSHER METHOD, natural products, NMR, PHYSICOCHEMICAL, PROPERTIES, SECONDARY ALCOHOLS, SPIN-COUPLING CONSTANTS, STEREOCHEMISTRY},
	isbn = {1433-7851},
	url = {<Go to ISI>://000225337000017},
	author = {MacMillan, J. B. and Linington, R. G. and Andersen, R. J. and Molinski, T. F.}
}
@article {337,
	title = {Tupuseleiamides and basiliskamides, new acyldipeptides and antifungal polyketides produced in culture by a Bacillus laterosporus isolate obtained from a tropical marine habitat},
	journal = {Journal of Natural Products},
	volume = {65},
	number = {10},
	year = {2002},
	note = {ISI Document Delivery No.: 609YZTimes Cited: 13Cited Reference Count: 14},
	month = {Oct},
	pages = {1447-1451},
	type = {Article},
	abstract = {Laboratory cultures of PNG 276, a Bacillus laterosporus isolate obtained from coastal waters off Papua New Guinea, have been shown to produce the novel metabolites basiliskamide A (1), basiliskamide B (2), tupuseleiamide A (3), and tupusleiamide B (4). The structures of I to 4 were elucidated by analysis of spectroscopic data and chemical degradation. Basiliskamides A (1) and B (g) show potent in vitro anti-Candida, activity.},
	keywords = {ANTIBIOTIC-RESISTANCE, BACTERIUM, MICROORGANISMS, NATURAL-PRODUCTS, STEREOCHEMISTRY, YM-47522},
	isbn = {0163-3864},
	url = {<Go to ISI>://000178935100011},
	author = {Barsby, T. and Kelly, M. T. and Andersen, R. J.}
}
@article {3625,
	title = {Synthesis of meso-phenyl-4,6-dipyrrins, preparation of their Cu(II), Ni(II), and Zn(II) chelates, and structural characterization of bis[meso-phenyl-4,6-dipyrrinato]Ni(II)},
	journal = {Canadian Journal of Chemistry-Revue Canadienne De Chimie},
	volume = {74},
	number = {11},
	year = {1996},
	note = {ISI Document Delivery No.: WC124Times Cited: 73Cited Reference Count: 58},
	month = {Nov},
	pages = {2182-2193},
	type = {Article},
	abstract = {{meso-Phenyldipyrromethanes can be oxidized by 2,6-dicyano-3,5-dichloro-para-benzoquinone (DDQ) to the corresponding meso-phenyldipyrrins. As expected, these novel, stable bipyrrolic pigments readily form metal chelates with copper(II), nickel(II), and zinc(II). Their W-VIS spectra are compared with a series of blown alkyl-substituted dipyrrin chelates and, based oil the W-VIS spectral analysis, the dihedral angle between the two ligands iri the bis[meso-phenyldipyrrinato]Ni(II) complex was calculated to be 42 degrees. The molecular structure of this complex was determined by X-ray crystallography, essentially confirming the calculation. Crystals of C30H22N4Ni are orthorhombic},
	keywords = {CRYSTAL-STRUCTURE, DIPYRROMETHENES, LIGANDS, meso-phenyldipyrrinato transition metal chelates, meso-phenyldipyrrins, meso-phenyldipyrromethanes, MOLECULAR, PYRROLE PIGMENTS, STEREOCHEMISTRY, TRANSITION-METAL COMPLEXES, X-RAY CRYSTALLOGRAPHY},
	isbn = {0008-4042},
	url = {<Go to ISI>://A1996WC12400032},
	author = {Bruckner, C. and Karunaratne, V. and Rettig, S. J. and Dolphin, D.}
}
@article {3643,
	title = {Synthesis of some phosphino- and arsinobenzenechromium tricarbonyl derivatives and metal carbonyl clusters},
	journal = {Canadian Journal of Chemistry-Revue Canadienne De Chimie},
	volume = {74},
	number = {11},
	year = {1996},
	note = {ISI Document Delivery No.: WC124Times Cited: 6Cited Reference Count: 36},
	month = {Nov},
	pages = {2167-2181},
	type = {Article},
	abstract = {{The synthesis of a number of new phosphino- and arsinobenzenechromium tricarbonyl ligands ER(2)C(6)H(5)Cr(CO)(3) (ER(2) = PEt(2), PPr2i, PBu(2)(t), PPh(2), AsPh(2) AsMe(2)), ER[C6H5Cr(CO)(3)](2) (ER = PEt, PBu(t), PPh, AsPh) has been achieved by reacting lithium derivatives of benzenechromium tricarbonyl with appropriate chlorophosphines or iodoarsines. The spectroscopic properties of these ligands are described. The structure of (Pr2PC6H5Cr)-P-i(CO)(3) was determined by an X-ray crystallographic study. This is the first solid state structure to be reported for a phosphinobenzenechromium tricarbonyl derivative. The structures of four metal carbonyl cluster complexes were also determined. Crystals of (Pr2PC6H5Cr)-P-i(CO)(3) (3, C15H19CrO3P) are monoclinic, space group P2(1)/c},
	keywords = {(BENZYNE)CHROMIUM, arsinobenzenechromium tricarbonyl derivatives, CHEMISTRY, COMPLEXES, CRYSTAL, DERIVATIVES, LIGAND-SUBSTITUTED DERIVATIVES, metal carbonyl clusters, OS3(CO)12, P(OCH2CF3)3, phosphinobenzenechromium tricarbonyl, RU3(CO)12, STEREOCHEMISTRY, structures, TRICARBONYL, X-ray structures},
	isbn = {0008-4042},
	url = {<Go to ISI>://A1996WC12400031},
	author = {Cullen, W. R. and Rettig, S. J. and Zhang, H. L.}
}
@article {2775,
	title = {THE SYNTHESIS AND X-RAY STRUCTURES OF THE GEOMETRIC ISOMERS OF 1-AMINO-1,2-CYCLOPENTANEDICARBOXYLIC ACID},
	journal = {Canadian Journal of Chemistry-Revue Canadienne De Chimie},
	volume = {71},
	number = {1},
	year = {1993},
	note = {ISI Document Delivery No.: KN060Times Cited: 5Cited Reference Count: 9},
	month = {Jan},
	pages = {76-83},
	type = {Article},
	abstract = {The geometric isomers of 1-amino-1,2-cyclopentanedicarboxylic acid were isolated as the hydrolysis products of 2-cyclopentanecarboxylic acid-5,5{\textquoteright}-hydantoin. The hydantoin ester was formed from ethyl -2-oxocyclopentanecarboxylate via a Bucherer-Bergs reaction. Hydrolysis of the hydantoin at elevated temperatures gave a mixture of trans- and cis-1-amino-1,2-cyclopentanedicarboxylic acids indicating epimerization during hydrolysis. The trans product has not been described previously and the cis not extensively characterized. X-ray crystallography reveals that both isomers are zwitterionic in the solid state and the cis isomer molecules are linked by unusually strong hydrogen bonding. Structures were confirmed by C-13 NMR, X-ray crystallography, and elemental analysis. Physical data are also presented.},
	keywords = {BUCHERER-BERGS, NEURONS, STEREOCHEMISTRY, STRECKER REACTIONS},
	isbn = {0008-4042},
	url = {<Go to ISI>://A1993KN06000011},
	author = {Curry, K. and McLennan, H. and Rettig, S. J. and Trotter, J.}
}
@article {7369,
	title = {SYNTHESIS AND CHARACTERIZATION OF DERIVATIZED CAPPED PORPHYRINS},
	journal = {Canadian Journal of Chemistry-Revue Canadienne De Chimie},
	volume = {70},
	number = {5},
	year = {1992},
	note = {ISI Document Delivery No.: JL870Times Cited: 4Cited Reference Count: 31},
	month = {May},
	pages = {1366-1374},
	type = {Article},
	abstract = {{The syntheses of porphyrins carrying either a fully hydrophobic cavity with a benzene moiety (32a,b) or a polar cavity with an amidobenzene (32c-d) are described. Terephthaldehyde (1) was converted to benzene-bisalkanoic acids (8, 10) and nitrobenzene-bisalkanoic acids (13 and 16) by using standard methods. The corresponding diacid chlorides 17a-d were used to acylate two equivalents of a beta-unsubstituted pyrrole, and the ketonic groups were reduced by diborane. Following the transformation of the nitro function to the acetamide, appropriate modifications of the ethyl ester functions afforded the key bisformylpyrroles 25a-d. The cyanoacrylate-protected formyl pyrrole derivatives were mono-chlorinated at the alpha-methyl groups and condensed with two equivalents of an alpha-unsubstitutued pyrrole to give the dipyrromethane dimers. Strong aqueous alkali caused saponification of the two ester groups and deprotection of the formyl functions to produce the dipyrromethane dimer 30, which, after thermal decarboxylation, was cyclized intramolecularly in acidic medium to give the porphyrins 32 (n = 4 or 5},
	keywords = {BINDING, CO, HUMAN OXYHEMOGLOBIN, IRON(II), O-2, RESOLUTION, STEREOCHEMISTRY},
	isbn = {0008-4042},
	url = {<Go to ISI>://A1992JL87000017},
	author = {Tang, H. and Wijesekera, T. P. and Dolphin, D.}
}
