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Journal of Experimental Botany May 2016Photorespiration is one of the major carbon metabolism pathways in oxygen-producing photosynthetic organisms. This pathway recycles 2-phosphoglycolate (2-PG), a toxic... (Review)
Review
Photorespiration is one of the major carbon metabolism pathways in oxygen-producing photosynthetic organisms. This pathway recycles 2-phosphoglycolate (2-PG), a toxic metabolite, to 3-phosphoglycerate when ribulose-1,5-bisphosphate carboxylase/oxygenase (RuBisCO) uses oxygen instead of carbon dioxide. The photorespiratory cycle is in competition with photosynthetic CO2 fixation and it is accompanied by carbon, nitrogen and energy losses. Thus, photorespiration has become a target to improve crop yields. Moreover, during the photorespiratory cycle intermediate metabolites that are toxic to Calvin-Benson cycle and RuBisCO activities, such as 2-PG, glycolate and glyoxylate, are produced. Thus, the presence of an efficient 2-PG/glycolate/glyoxylate 'detoxification' pathway is required to ensure normal development of photosynthetic organisms. Here we review our current knowledge concerning the enzymes that carry out the glycolate-glyoxylate metabolic steps of photorespiration from glycolate production in the chloroplasts to the synthesis of glycine in the peroxisomes. We describe the properties of the proteins involved in glycolate-glyoxylate metabolism in Archaeplastida and the phenotypes observed when knocking down/out these specific photorespiratory players. Advances in our understanding of the regulation of glycolate-glyoxylate metabolism are highlighted.
Topics: Chloroplasts; Glycolates; Glyoxylates; Peroxiredoxins; Photosynthesis; Plant Development; Plant Physiological Phenomena; Plants
PubMed: 26994478
DOI: 10.1093/jxb/erw090 -
Advances in Experimental Medicine and... 2017Euglenoids are able to assimilate fatty acids and alcohols with various carbon-chain lengths, and ethanol is known to be one of the best carbon sources to support the... (Review)
Review
Euglenoids are able to assimilate fatty acids and alcohols with various carbon-chain lengths, and ethanol is known to be one of the best carbon sources to support the growth of Euglena gracilis. Ethanol is first oxidized to acetate by the sequential reactions of alcohol dehydrogenase and acetaldehyde dehydrogenase in the mitochondria, and then converted to acetyl coenzyme A (acetyl-CoA). Acetyl-CoA is metabolized through the glyoxylate cycle which is a modified tricarboxylic acid (TCA) cycle in which isocitrate lyase (ICL) and malate synthase (MS) function to bypass the two decarboxylation steps of the TCA cycle, enabling the net synthesis of carbohydrates from C2 compounds. ICL and MS form a unique bifunctional enzyme localized in Euglena mitochondria, not in glyoxysome as in other eukaryotes. The unique glyoxylate and glycolate metabolism during photorespiration is also discussed in this chapter.
Topics: Acetic Acid; Citric Acid Cycle; Ethanol; Euglena; Glycolates; Glyoxylates; Mitochondria
PubMed: 28429316
DOI: 10.1007/978-3-319-54910-1_3 -
Indian Journal of Dermatology,... 2013
Topics: Alkaptonuria; Glycolates; Humans; Male; Middle Aged; Ochronosis
PubMed: 23760323
DOI: 10.4103/0378-6323.113086 -
Journal of the American Chemical Society Mar 2017Enantioconvergent arylation reactions of boronic acids and racemic β-stereogenic α-keto esters have been developed. The reactions are catalyzed by a chiral...
Enantioconvergent arylation reactions of boronic acids and racemic β-stereogenic α-keto esters have been developed. The reactions are catalyzed by a chiral (diene)Rh(I) complex and provide a wide array of β-stereogenic tertiary aryl glycolate derivatives with high levels of diastereo- and enantioselectivity. Racemization studies employing a series of sterically differentiated tertiary amines suggest that the steric nature of the amine base additive exerts a significant influence on the rate of substrate racemization.
Topics: Esters; Glycolates; Ketones; Molecular Structure; Stereoisomerism
PubMed: 28252953
DOI: 10.1021/jacs.7b00943 -
Topics in Current Chemistry 2014The development of sustainable chemical processes for the conversion of highly oxygenated biomass feedstocks to chemical products requires efficient and selective... (Review)
Review
The development of sustainable chemical processes for the conversion of highly oxygenated biomass feedstocks to chemical products requires efficient and selective processes for partial oxygen removal and refunctionalization. Here we review the development of the deoxydehydration (DODH) reaction, which converts vicinal diols (glycols) to olefins. Uncatalyzed deoxygenative eliminations were first established. The catalyzed DODH reactions have largely employed oxo-rhenium catalysts and a variety of reductants, including PR₃, dihydrogen, sulfite, and alcohols. A variety of glycol and biomass-derived polyol substrates undergo the DODH reaction in moderate to good efficiency, regioselectively, and stereoselectively. Observations regarding selectivity, mechanistic probes, and computational studies support the general operation of a catalytic process involving three basic stages: glycol condensation to an M-glycolate, reduction of the oxo-metal, glycol condensation to produce a metal-glycolate, and alkene extrusion from the reduced metal-glycolate. Recent practical developments include the discovery of non-precious V- and Mo-oxo DODH catalysis.
Topics: Alcohols; Alkenes; Biomass; Catalysis; Glycolates; Glycols; Oxidation-Reduction; Oxygen; Reducing Agents; Rhenium; Stereoisomerism; Thermodynamics
PubMed: 24756633
DOI: 10.1007/128_2014_537 -
Mutation Research Oct 1997The available data on the genotoxicity of 2-butoxyethanol have been reviewed. 2-Butoxyethanol has been examined for genotoxic activity in a range of in vitro and in vivo... (Review)
Review
The available data on the genotoxicity of 2-butoxyethanol have been reviewed. 2-Butoxyethanol has been examined for genotoxic activity in a range of in vitro and in vivo assays, including the mouse bone marrow micronucleus assay. The in vitro assays used range from well validated and generally accepted assays such as the Salmonella/microsome and in vitro cytogenetic assay, through to less well validated assays such as assessment of the inhibition of metabolic cooperation in V79 cells. The levels of experimental details and data reporting vary across the studies with some papers presenting only limited information. Taking the above factors into consideration, the available data indicate that 2-butoxyethanol has no significant genotoxic activity. This conclusion is also consistent with the chemical structure of 2-butoxyethanol, which is not alerting for likely genotoxic activity. These collected considerations indicate that 2-butoxyethanol is unlikely to be a genotoxic carcinogen to rodents, a prediction that supplements seventeen published predictions of the outcome of the ongoing NTP rodent carcinogenicity bioassays.
Topics: Acetaldehyde; Animals; Ethylene Glycols; Female; Glycolates; Humans; Male; Mutagenicity Tests; Mutagens; Mutation
PubMed: 9372852
DOI: 10.1016/s1383-5742(97)00025-2 -
Chemical Communications (Cambridge,... Nov 2022Methyl vinyl glycolate (MVG) can be obtained by acid-catalyzed conversion of C4 and C6 sugars. Applications of MVG in polymers are so far limited to its use as...
Methyl vinyl glycolate (MVG) can be obtained by acid-catalyzed conversion of C4 and C6 sugars. Applications of MVG in polymers are so far limited to its use as co-monomer for poly(lactic acid) and as crosslinking agent. In this work, hydroformylation and methoxycarbonylation of MVG were investigated to produce novel bifunctional monomers. Polyesters with high renewable-atom content were successfully prepared and characterized.
Topics: Polyesters; Glycolates; Polymers; Polyvinyl Chloride
PubMed: 36342084
DOI: 10.1039/d2cc05609g -
Current Opinion in Biotechnology Feb 2024Single-carbon (C1) biorefinery plays a key role in the consumption of global greenhouse gases and a circular carbon economy. Thereby, we have focused on the valorization... (Review)
Review
Single-carbon (C1) biorefinery plays a key role in the consumption of global greenhouse gases and a circular carbon economy. Thereby, we have focused on the valorization of C1 compounds (e.g. methanol, formaldehyde, and formate) into multicarbon products, including bioplastic monomers, glycolate, and ethylene glycol. For instance, methanol, derived from the oxidation of CH, can be converted into glycolate, ethylene glycol, or erythrulose via formaldehyde and glycolaldehyde, employing C1 and/or C2 carboligases as essential enzymes. Escherichia coli was engineered to convert formate, produced from CO via CO or from CO directly, into glycolate. Recent progress in the design of biotransformation pathways, enzyme discovery, and engineering, as well as whole-cell biocatalyst engineering for C1 biorefinery, was addressed in this review.
Topics: Methanol; Carbon; Carbon Dioxide; Ethylene Glycol; Escherichia coli; Formates; Formaldehyde; Glycolates
PubMed: 38128199
DOI: 10.1016/j.copbio.2023.103047 -
Clinics in Dermatology 2009The hydroxyacids are represented by the alpha-hydroxyacids, beta-hydroxyacids, polyhydroxy acids, and bionic acids. Together, these ingredients form a class of compounds... (Review)
Review
The hydroxyacids are represented by the alpha-hydroxyacids, beta-hydroxyacids, polyhydroxy acids, and bionic acids. Together, these ingredients form a class of compounds with unparalleled benefits to the skin and unprecedented usage in the cosmeceutical market in cosmetic and therapeutic formulations alike. The most commonly used hydroxyacid is glycolic acid, an alpha-hydroxyacid that has been used extensively in cosmetic antiaging formulations, moisturizers, and peels, and in treatment products to improve hyperpigmentation and acne. The newer polyhydroxy and bionic acids offer the benefits of alpha-hydroxyacids without irritation, making them suitable for use on sensitive skin, rosacea, and after cosmetic procedures. They also provide additional antioxidant/chelation, barrier strengthening, and moisturizing effects. Bionic acids inhibit matrix metalloproteinase enzymes in skin, providing a preventative antiaging benefit. The hydroxyacids as a class can be combined with therapeutically active materials and cosmetic procedures to increase therapeutic effects and improve tolerability and outcomes of medicinal agents and procedures.
Topics: Acne Vulgaris; Administration, Cutaneous; Biological Availability; Cosmetics; Dermatologic Agents; Female; Glycolates; Humans; Hydroxy Acids; Male; Psoriasis; Rosacea; Skin Absorption; Skin Diseases; Treatment Outcome
PubMed: 19695482
DOI: 10.1016/j.clindermatol.2009.06.023 -
Cleveland Clinic Journal of Medicine Jun 1997Frequent and daily use of cosmetic and skin-care products that contain alpha-hydroxy acids (AHAs) moisturizes the skin and produces smoother, less-wrinkled skin... (Review)
Review
Frequent and daily use of cosmetic and skin-care products that contain alpha-hydroxy acids (AHAs) moisturizes the skin and produces smoother, less-wrinkled skin surfaces. The cosmetic products developed as astringents and exfoliants diminish skin scales and remove excess skin oil. New studies suggest that photodamaged skin improves with AHA treatment.
Topics: Beauty Culture; Chemistry, Pharmaceutical; Drug Prescriptions; Glycolates; Humans; Lactic Acid; Nonprescription Drugs; Skin Aging
PubMed: 9188214
DOI: 10.3949/ccjm.64.6.327