scholarly journals Rhodoxanthin synthase from honeysuckle; a membrane diiron enzyme catalyzes the multistep conversation of β-carotene to rhodoxanthin

2020 ◽  
Vol 6 (17) ◽  
pp. eaay9226
Author(s):  
John Royer ◽  
John Shanklin ◽  
Nathalie Balch-Kenney ◽  
Maria Mayorga ◽  
Peter Houston ◽  
...  
Keyword(s):  
Double Bond ◽  
Biosynthetic Pathway ◽  
Catalytic Cycle ◽  
Carotenoid Pigments ◽  
Double Bonds ◽  
Plant Kingdom ◽  
Multifunctional Enzyme ◽  
Type Integral ◽  
Diiron Enzyme ◽  
Β Carotene

Rhodoxanthin is a vibrant red carotenoid found across the plant kingdom and in certain birds and fish. It is a member of the atypical retro class of carotenoids, which contain an additional double bond and a concerted shift of the conjugated double bonds relative to the more widely occurring carotenoid pigments, and whose biosynthetic origins have long remained elusive. Here, we identify LHRS (Lonicera hydroxylase rhodoxanthin synthase), a variant β-carotene hydroxylase (BCH)–type integral membrane diiron enzyme that mediates the conversion of β-carotene into rhodoxanthin. We identify residues that are critical to rhodoxanthin formation by LHRS. Substitution of only three residues converts a typical BCH into a multifunctional enzyme that mediates a multistep pathway from β-carotene to rhodoxanthin via a series of distinct oxidation steps in which the product of each step becomes the substrate for the next catalytic cycle. We propose a biosynthetic pathway from β-carotene to rhodoxanthin.

MNDO CI study of the photoisomerization of pentadieniminium

1990 ◽  
Vol 55 (12) ◽  
pp. 2874-2879 ◽  
Author(s):  
Peter Ertl
Keyword(s):  
Schiff Base ◽  
Double Bond ◽  
Configuration Interaction ◽  
Mndo Method ◽  
Double Bonds

Photoisomerization mechanism in model retinal-like protonated Schiff base pentadieniminium was investigated by using MNDO method with configuration interaction. Isomerizations around various double bonds were studied and twisted biradical geometries in S0 and S1 states were optimized. Photoisomerization proceeds exclusively around the central double bond where the twisted S1 state is strongly stabilized and the S0-S1 gap is minimal.

scholarly journals Carotenoids from Cyanobacteria: Biotechnological Potential and Optimization Strategies

Biomolecules ◽  
2021 ◽  
Vol 11 (5) ◽  
pp. 735
Author(s):  
Fernando Pagels ◽  
Vitor Vasconcelos ◽  
Ana Catarina Guedes
Keyword(s):  
Energy Dissipation ◽  
Industrial Production ◽  
Protein Complex ◽  
Biosynthetic Pathway ◽  
Environmentally Friendly ◽  
Potential Candidate ◽  
Biotechnological Potential ◽  
Photosynthetic Organisms ◽  
Orange Carotenoid Protein ◽  
Β Carotene

Carotenoids are tetraterpenoids molecules present in all photosynthetic organisms, responsible for better light-harvesting and energy dissipation in photosynthesis. In cyanobacteria, the biosynthetic pathway of carotenoids is well described, and apart from the more common compounds (e.g., β-carotene, zeaxanthin, and echinenone), specific carotenoids can also be found, such as myxoxanthophyll. Moreover, cyanobacteria have a protein complex called orange carotenoid protein (OCP) as a mechanism of photoprotection. Although cyanobacteria are not the organism of choice for the industrial production of carotenoids, the optimisation of their production and the evaluation of their bioactive capacity demonstrate that these organisms may indeed be a potential candidate for future pigment production in a more environmentally friendly and sustainable approach of biorefinery. Carotenoids-rich extracts are described as antioxidant, anti-inflammatory, and anti-tumoral agents and are proposed for feed and cosmetical industries. Thus, several strategies for the optimisation of a cyanobacteria-based bioprocess for the obtention of pigments were described. This review aims to give an overview of carotenoids from cyanobacteria not only in terms of their chemistry but also in terms of their biotechnological applicability and the advances and the challenges in the production of such compounds.

A stereospecific synthesis of trisubstituted double bonds

1970 ◽  
Vol 23 (4) ◽  
pp. 813 ◽  
Author(s):  
AJ Birch ◽  
B McKague
Keyword(s):  
Double Bond ◽  
Stereospecific Synthesis ◽  
Considerable Proportion ◽  
Double Bonds ◽  
Steric Configuration

An aspect of the synthesis of sterically defined trisubstituted double bonds is discussed. Metal-ammonia reductions of hydropyridinium salts such as (1 ; R, R' = H or Me) result in allylic fissions, with a considerable proportion of double bond retention in its original situation and complete retention of the original steric configuration in that position.

Chlorination of Natural Rubber in Solution with Gaseous Chlorine

1953 ◽  
Vol 26 (4) ◽  
pp. 902-911 ◽  
Author(s):  
C. S. Ramakrishnan ◽  
D. Raghunath ◽  
J. B. Pande
Keyword(s):  
Double Bond ◽  
Natural Rubber ◽  
Cyclization Reaction ◽  
Double Bonds ◽  
Chlorine Atoms ◽  
Reaction Stage ◽  
Stage 1 ◽  
Additive Reaction

Abstract The chlorination of rubber solutions by gaseous chlorine was followed by isolating the partially chlorinated products and preparing their ozonides. The ozonides were hydrolyzed, and the acids and aldehydes formed on hydrolysis were determined. By a comparison with the amounts of acids and aldehydes obtained from ozonides of unreacted rubber, the amount of residual isoprenic double bonds present was found. The loss of double bonds attending the introduction of chlorine atoms into the molecule of rubber indicates four definite stages in chlorination : (1) initial substitutive attack by chlorine, with concomitant cyclization, resulting in a loss of one double bond between two isoprenic units, (2) substitution, (3) additive reaction, and (4) essentially substitution. Chlorination of aged rubber solutions differs from the above in that the cyclization reaction (stage 1) seems to be absent.

scholarly journals Screening of carotenoid-producing Rhodotorula strains isolated from natural sources

2015 ◽  
Vol 8 (1) ◽  
pp. 34-38 ◽  
Author(s):  
Jana Tkáčová ◽  
Katarína Furdíková ◽  
Tatiana Klempová ◽  
Katarína Ďurčanská ◽  
Milan Čertík
Keyword(s):  
Positive Impact ◽  
Human Life ◽  
Carotenoid Pigments ◽  
High Demand ◽  
Natural Pigments ◽  
Feed Industry ◽  
Food And Feed ◽  
Petri Dishes ◽  
Pigment Accumulation ◽  
Β Carotene

Abstract Carotenoids represent large group of various natural pigments ensuring typical coloration of plants, microorganisms and several animals. It was confirmed by many studies, that consuming these biological active compounds has positive impact for human life. Therefore, they are applied in different industrial fields, such as pharmacy, cosmetic, food, and feed industry. Due to high demand for carotenoids we would like to discover new microorganisms overproducing carotenoids. We focused on yeasts of genus Rhodotorula sp. (forty isolates), that we screened according to growth and carotenoid production on Petri dishes and production media. After cultivation on Petri dishes we selected five strains (denoted as KF-4, KF-6, KF-24, KF-31, KF-104) with interesting pigment production and quick growth. The secondary screening on production media identified KF-104 as the best producer of carotenoid pigments with massive pigment accumulation (1.15 mg/g DCW) and yield (9.69 mg/L). The main carotenoid of KF-104 isolate was β-carotene (35.4 %) with the accumulation of 408.7 μg/g DCW and the yield of 3.4 mg/L. The rest were torularhodin, torulene and γ-carotene (62.7–79.0 %). Production of torularhodin in the cells was low (0.4 to 1.4 mg/L) as was its accumulation in cells (31.2–121.0 μg/g DCW). We continue the experimental analyses of these isolates in order understand differences in the content of individual pigments.

The Change in the Raman Spectra of Chloroprene and Isoprene in the Polymerization Process

1943 ◽  
Vol 16 (4) ◽  
pp. 841-847
Author(s):  
A. Gantmacher ◽  
S. Medvedev
Keyword(s):  
Raman Spectrum ◽  
Double Bond ◽  
Raman Spectra ◽  
Polymer Molecule ◽  
Polymerization Process ◽  
High Polymer ◽  
Single Bond ◽  
Double Bonds ◽  
Continuous Background ◽  
Single Bonds

Abstract 1. When chloroprene and isoprene polymerize, besides the frequency characterizing the conjugate double bond in the monomer, there appears a higher frequency corresponding to the isolated double bond in the polymer. In the polymerization process, the intensity of the frequency of the conjugate double bond decreases and the intensity of the frequency of the isolated double bond increases. Because of the increase in the number of single bonds in the polymer, the intensity of the frequency of the single bond 1005 in the polymer is considerably greater than in the monomer. 2. Even in the case of the samples with high polymer contents (greater than 50 per cent), the intensity of the frequency of the conjugate double bond is considerably greater than the intensity of the frequency of the isolated double bond. This is attributable to the fact that part of double bonds disappear during polymerization. 3. The Raman spectra of the chloroprene and isoprene polymers differ essentially from those of the monomers. To characterize the frequencies of vibration in the polymer molecule, it is essential to investigate its Raman spectrum in a medium free of the monomer. 4. The formation of highly polymeric molecules on polymerization does not result in an increase in the intensity of the continuous background in spectrograms.

Mechanisms of Nucleophilic Attack at Carbon Nitrogen Double-Bonds: The Reaction of Benzohydrazonoyl Halides With Amines

1987 ◽  
Vol 40 (10) ◽  
pp. 1777 ◽  
Author(s):  
AF Hegarty ◽  
P Rigopoulos ◽  
JE Rowe
Keyword(s):  
Double Bond ◽  
Nucleophilic Attack ◽  
Rate Data ◽  
Double Bonds ◽  
Nitrogen Double Bond

Rate data for the reaction of a series of benzohydrazonoyl halides with pyrrolidine and butan- 1-amine at 303 K are presented. Linear Hammett plots were obtained with each amine. The mechanism of the reactions and the stereochemical outcome of these displacements at the carbon-nitrogen double bond are discussed.

scholarly journals Phenolation of vegetable oils

2011 ◽  
Vol 76 (4) ◽  
pp. 591-606 ◽  
Author(s):  
Mihail Ionescu ◽  
Zoran Petrovic
Keyword(s):  
Fatty Acids ◽  
Oleic Acid ◽  
Double Bond ◽  
Vegetable Oils ◽  
Raw Materials ◽  
Complex Mixture ◽  
Double Bonds ◽  
Triflic Acid ◽  
Model Compounds ◽  
Phenol Alkylation

Novel bio-based compounds containing phenols suitable for the synthesis of polyurethanes were prepared. The direct alkylation of phenols with different vegetable oils in the presence of superacids (HBF4, triflic acid) as catalysts was studied. The reaction kinetics was followed by monitoring the decrease of the double bond content (iodine value) with time. In order to understand the mechanism of the reaction, phenol was alkylated with model compounds. The model compounds containing one internal double bond were 9-octadecene and methyl oleate and those with three double bonds were triolein and high oleic safflower oil (82% oleic acid). It was shown that the best structures for phenol alkylation are fatty acids with only one double bond (oleic acid). Fatty acids with two double bonds (linoleic acid) and three double bonds (linolenic acid) lead to polymerized oils by a Diels Alder reaction, and to a lesser extent to phenol alkylated products. The reaction product of direct alkylation of phenol with vegetable oils is a complex mixture of phenol alkylated with polymerized oil (30-60%), phenyl esters formed by transesterification of phenol with triglyceride ester bonds (<10 %) and unreacted oil (30%). The phenolated vegetable oils are new aromatic-aliphatic bio-based raw materials suitable for the preparation of polyols (by propoxylation, ethoxylation, Mannich reactions) for the preparation of polyurethanes, as intermediates for phenolic resins or as bio-based antioxidants.

Structural Homogeneity in Unsaturated Fatty Acids of Marine Lipids. A Review

1964 ◽  
Vol 21 (2) ◽  
pp. 247-254 ◽  
Author(s):  
R. G. Ackman
Keyword(s):  
Fatty Acids ◽  
Double Bond ◽  
Polyunsaturated Fatty Acids ◽  
Chain Length ◽  
Unsaturated Fatty Acids ◽  
Analytical Data ◽  
Double Bonds ◽  
Marine Origin ◽  
Methyl Group ◽  
Marine Lipids

Consideration of recent analytical data supports the conclusion that the longer-chain polyunsaturated fatty acids of marine origin are all structurally homogeneous in that the double bonds are cis, the double bonds methylene interrupted, and that, with the exception of the C16 chain length, the ultimate double bond will normally be three, six or nine carbon atoms removed from the terminal methyl group.

scholarly journals Oxepinamide F biosynthesis involves enzymatic d-aminoacyl epimerization, 3H-oxepin formation, and hydroxylation induced double bond migration

2020 ◽  
Vol 11 (1) ◽  
Author(s):  
Liujuan Zheng ◽  
Haowen Wang ◽  
Aili Fan ◽  
Shu-Ming Li
Keyword(s):  
Cytochrome P450 ◽  
Double Bond ◽  
Biosynthetic Pathway ◽  
Hydroxyl Group ◽  
Cytochrome P450 Enzyme ◽  
Double Bond Migration ◽  
Feeding Experiments ◽  
Aspergillus Ustus ◽  
P450 Enzyme ◽  
Derivatives Of

Abstract Oxepinamides are derivatives of anthranilyl-containing tripeptides and share an oxepin ring and a fused pyrimidinone moiety. To the best of our knowledge, no studies have been reported on the elucidation of an oxepinamide biosynthetic pathway and conversion of a quinazolinone to a pyrimidinone-fused 1H-oxepin framework by a cytochrome P450 enzyme in fungal natural product biosynthesis. Here we report the isolation of oxepinamide F from Aspergillus ustus and identification of its biosynthetic pathway by gene deletion, heterologous expression, feeding experiments, and enzyme assays. The nonribosomal peptide synthase (NRPS) OpaA assembles the quinazolinone core with d-Phe incorporation. The cytochrome P450 enzyme OpaB catalyzes alone the oxepin ring formation. The flavoenzyme OpaC installs subsequently one hydroxyl group at the oxepin ring, accompanied by double bond migration. The epimerase OpaE changes the d-Phe residue back to l-form, which is essential for the final methylation by OpaF.

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