@article {2113, title = {Plant surface lipid biosynthetic pathways and their utility for metabolic engineering of waxes and hydrocarbon biofuels}, journal = {Plant Journal}, volume = {54}, number = {4}, year = {2008}, note = {ISI Document Delivery No.: 299KRTimes Cited: 12Cited Reference Count: 122Jetter, Reinhard Kunst, Ljerka}, month = {May}, pages = {670-683}, type = {Review}, abstract = {Due to their unique physical properties, waxes are high-value materials that are used in a variety of industrial applications. They are generated by chemical synthesis, extracted from fossil sources, or harvested from a small number of plant and animal species. As a result, the diversity of chemical structures in commercial waxes is low and so are their yields. These limitations can be overcome by engineering of wax biosynthetic pathways in the seeds of high-yielding oil crops to produce designer waxes for specific industrial end uses. In this review, we first summarize the current knowledge regarding the genes and enzymes generating the chemical diversity of cuticular waxes that accumulate at the surfaces of primary plant organs. We then consider the potential of cuticle biosynthetic genes for biotechnological wax production, focusing on selected examples of wax ester chain lengths and isomers. Finally, we discuss the genes/enzymes of cuticular alkane biosynthesis and their potential in future metabolic engineering of plants for the production of renewable hydrocarbon fuels.}, keywords = {ARABIDOPSIS-THALIANA, BRASSICA-OLERACEA, chain lengths, CONDENSING ENZYME, CUTICULAR WAX, cuticular waxes, ECERIFERUM MUTANTS, EPICUTICULAR WAX, ESTERS, fatty acid elongation, FATTY ACYL-COENZYME, HYDROCARBONS, industrial products, LEAVES PISUM-SATIVUM, MOLECULAR CHARACTERIZATION, SACCHAROMYCES-CEREVISIAE}, isbn = {0960-7412}, url = {://000255755000012}, author = {Jetter, R. and Kunst, L.} } @article {1034, title = {A convenient method for the conversion of hindered carboxylic acids to N-methoxy-N-methyl (Weinreb) amides}, journal = {Journal of Organic Chemistry}, volume = {69}, number = {25}, year = {2004}, note = {ISI Document Delivery No.: 877EJTimes Cited: 14Cited Reference Count: 35}, month = {Dec}, pages = {8984-8986}, type = {Article}, abstract = {The conversion of sterically hindered carboxylic acids to N-methoxy-N-methyl amides can be efficiently carried out with 1.1 equiv of methanesulfonyl chloride, 3 equiv of triethylamine, and 1.1 equiv of N-methoxy-N-methylamine. Yields for this process range from 59\% to 88\%. The major byproduct in these reactions, N-methoxy-N-methylmethanesulfonamide, can be removed by placing the product mixture under vacuum for 14-24 h.}, keywords = {CHEMISTRY, CHLORIDE, ESTERIFICATION, ESTERS, GROUP ACTIVATION, lactones, MILD, REAGENT}, isbn = {0022-3263}, url = {://000225550300061}, author = {Woo, J. C. S. and Fenster, E. and Dake, G. R.} } @article {4840, title = {The influence of chiral auxiliaries is enhanced within zeolites}, journal = {Tetrahedron Letters}, volume = {41}, number = {43}, year = {2000}, note = {ISI Document Delivery No.: 368NKTimes Cited: 18Cited Reference Count: 20}, month = {Oct}, pages = {8231-8235}, type = {Article}, abstract = {Zeolites significantly enhance the influence of chiral auxiliaries during photochemical reactions. The generality of this phenomenon has been tested with three independent examples. Chiral auxiliaries that lead to 1:1 mixtures of diastereomers in solution give products in up to 80\% diastereomeric excess in the presence of faujasite type zeolites. (C) 2000 Elsevier Science Ltd. All rights reserved.}, keywords = {ASYMMETRIC PHOTOCHEMICAL-REACTIONS, ESTERS, INDUCTION, MODEL, SOLID-STATE}, isbn = {0040-4039}, url = {://000090123600010}, author = {Jayaraman, S. and Uppili, S. and Natarajan, A. and Joy, A. and Chong, K. C. W. and Netherton, M. R. and Zenova, A. and Scheffer, J. R. and Ramamurthy, V.} } @article {4610, title = {The metabolites of dietary chlorophylls}, journal = {Phytochemistry}, volume = {50}, number = {2}, year = {1999}, note = {ISI Document Delivery No.: 160EBTimes Cited: 15Cited Reference Count: 70}, month = {Jan}, pages = {195-202}, type = {Review}, abstract = {Chlorophylls, the green pigments responsible for photosynthesis in plants, algae and bacteria, are also part of the daily diet of herbivorous feeders. Numerous metabolic derivatives of the major green pigment, chlorophyll-a, have been found in a wide variety of organisms during the last decade. Studies of these metabolites show that some are antioxidants or cellular signaling mediators in vivo. The metabolites of bacteriochlorophylls-c and d, recently found in the deep-sea dragon fish, Malacosteus niger, function as a visual photosensitizer, enabling the fish to seek their prey in {\textquoteright}the dark{\textquoteright}. Discovery of these metabolites as well as their interesting biological functions raises questions as to the roles of chlorophyll derivatives in the chemical ecology of herbivorous life forms. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.}, keywords = {antioxidant, AUTOXIDATION, cell signaling, CHLORIN, CHLOROPHYLL, DERIVATIVES, DIET, ESTERS, MARINE ORGANISMS, METABOLISM, PHOTOSENSITIZER, PI-CATION RADICALS, porphyrins, PRODUCTS, RUDITAPES-PHILIPPINARUM, TUNICHLORIN}, isbn = {0031-9422}, url = {://000078216500001}, author = {Ma, L. F. and Dolphin, D.} } @article {4063, title = {Chemical modification of chlorophyll a: Synthesis of new regiochemically pure benzoporphyrin and dibenzoporphyrin derivatives}, journal = {Canadian Journal of Chemistry-Revue Canadienne De Chimie}, volume = {75}, number = {3}, year = {1997}, note = {ISI Document Delivery No.: XD813Times Cited: 10Cited Reference Count: 28}, month = {Mar}, pages = {262-275}, type = {Article}, abstract = {Starting from pheophorbide a methyl ester (5), a degradation product of chlorophyll a, routes for the preparation of 3-vinylporphyrins 6 and 9 and of an [A,C]-divinylporphyrin 16 are described. These porphyrins were obtained as a result of chemical modification of 5 on ring D and the exocyclic ring E. Diels-Alder reactions of these (di)vinylporphyrins with dimethyl acetylenedicarboxylate, to afford new regiochemically pure benzoporphyrin derivatives 29 and 30 and dibenzoporphyrin derivative 33 for potential use as sensitizers in photodynamic therapy of tumors, were also investigated.}, keywords = {(di)benzoporphyrins, (di)vinylporphyrins, chlorins, CHLOROPHYLL, CONVERSION, Diels-Alder, ESTERS, photodynamic, PHOTODYNAMIC THERAPY, ROUTE, therapy}, isbn = {0008-4042}, url = {://A1997XD81300003}, author = {Ma, L. F. and Dolphin, D.} } @article {2874, title = {AN ENANTIOSPECIFIC SYNTHESIS OF 4-METHYLCAMPHOR}, journal = {Tetrahedron-Asymmetry}, volume = {4}, number = {11}, year = {1993}, note = {ISI Document Delivery No.: MJ468Times Cited: 10Cited Reference Count: 38}, month = {Nov}, pages = {2363-2370}, type = {Article}, abstract = {Treatment of (-)-2-methylenebornane (7), derived from (+)-camphor (1), with 45\% HBr /HOAc results in Wagner-Meerwein rearrangement and formation of 4-methylisobornyl bromide (17) in 80-90\% yield. The enantiopurity of (17) was determined by conversion to (+)-4-methylisoborneol (5) and (-)-4-methylcamphor (3).}, keywords = {CAMPHOR DERIVATIVES, ESTERS, KETONES, NATURAL PRODUCT SYNTHESIS, POTASSIUM, REARRANGEMENTS, ROUTE, STEROID-SYNTHESIS, SYNTHONS}, isbn = {0957-4166}, url = {://A1993MJ46800024}, author = {Money, T. and Palme, M. H.} }