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sophorose
2-O-beta-D-glucopyranosyl-D-glucose

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Name:(2R,3S,4R,5R)-3,4,5,6-tetrahydroxy-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhexanal
CAS Number: 534-46-3Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:208-600-6
FDA UNII: ZHQ3C30OP1
Nikkaji Web:J278.897G
XlogP3-AA:-5.00 (est)
Molecular Weight:342.29854000
Formula:C12 H22 O11
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
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Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Boiling Point: 783.70 °C. @ 760.00 mm Hg (est)
Flash Point: 558.00 °F. TCC ( 292.10 °C. ) (est)
logP (o/w): -4.340 (est)
Soluble in:
 water, 1e+006 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
alpha-sophorose
ExtraSynthese
For experimental / research use only.
alpha-Sophorose
 
Safety Information:
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for sophorose usage levels up to:
 not for fragrance use.
 
Recommendation for sophorose flavor usage levels up to:
 not for flavor use.
 
Safety References:
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Laboratory Chemical Safety Summary :92797
National Institute of Allergy and Infectious Diseases:Data
(2R,3S,4R,5R)-3,4,5,6-tetrahydroxy-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhexanal
Chemidplus:0000534463
 
References:
 (2R,3S,4R,5R)-3,4,5,6-tetrahydroxy-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhexanal
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):92797
Pubchem (sid):135049942
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
Golm Metabolome Database:Search
HMDB (The Human Metabolome Database):Search
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 found in nature
 
Synonyms:
2-O-beta-D-glucopyranosyl-D-glucose
2-O-beta-dextro-glucopyranosyl-dextro-glucose
(2R,3S,4R,5R)-3,4,5,6-tetrahydroxy-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhexanal
 

Articles:

PubMed:The antibiotic and membrane-damaging activities of cellobiose lipids and sophorose lipids.
PubMed:Comparative metabolism of cellulose, sophorose and glucose in Trichoderma reesei using high-throughput genomic and proteomic analyses.
PubMed:1,2-β-Oligoglucan phosphorylase from Listeria innocua.
PubMed:Structure elucidation and characterization of microbial 2-tridecyl sophorosides (biosurfactants).
PubMed:Expression pattern of cellulolytic and xylanolytic genes regulated by transcriptional factors XYR1 and CRE1 are affected by carbon source in Trichoderma reesei.
PubMed:Regulation of cellulase and hemicellulase gene expression in fungi.
PubMed:The role of CRE1 in nucleosome positioning within the cbh1 promoter and coding regions of Trichoderma reesei.
PubMed:Two major facilitator superfamily sugar transporters from Trichoderma reesei and their roles in induction of cellulase biosynthesis.
PubMed:Characterization of Ruminococcus albus cellodextrin phosphorylase and identification of a key phenylalanine residue for acceptor specificity and affinity to the phosphate group.
PubMed:Systems analysis of lactose metabolism in Trichoderma reesei identifies a lactose permease that is essential for cellulase induction.
PubMed:Characterization of a novel β-glucosidase from a compost microbial metagenome with strong transglycosylation activity.
PubMed:Mutation of the Xylanase regulator 1 causes a glucose blind hydrolase expressing phenotype in industrially used Trichoderma strains.
PubMed:Purification, gene cloning, and biochemical characterization of a β-glucosidase capable of hydrolyzing sesaminol triglucoside from Paenibacillus sp. KB0549.
PubMed:Promotion of extracellular lignocellulolytic enzymes production by restraining the intracellular β-glucosidase in Penicillium decumbens.
PubMed:Transepithelial transport of 6-O-caffeoylsophorose across Caco-2 cell monolayers.
PubMed:Xylanase XYN IV from Trichoderma reesei showing exo- and endo-xylanase activity.
PubMed:Design of selective production of sophorolipids by Rhodotorula bogoriensis through nutritional requirements.
PubMed:Re-annotation of the CAZy genes of Trichoderma reesei and transcription in the presence of lignocellulosic substrates.
PubMed:Identification of Bacillus selenitireducens MLS10 maltose phosphorylase possessing synthetic ability for branched α-D-glucosyl trisaccharides.
PubMed:Unusual, pH-induced, self-assembly of sophorolipid biosurfactants.
PubMed:Cytochrome P450 reductase from Candida apicola: versatile redox partner for bacterial P450s.
PubMed:Surface and biological activity of sophorolipid molecules produced by Wickerhamiella domercqiae var. sophorolipid CGMCC 1576.
PubMed:Structural characterization of novel sophorolipid biosurfactants from a newly identified species of Candida yeast.
PubMed:One-step production of unacetylated sophorolipids by an acetyltransferase negative Candida bombicola.
PubMed:Dehydrogenase GRD1 represents a novel component of the cellulase regulon in Trichoderma reesei (Hypocrea jecorina).
PubMed:Bioactivities of sophorolipid with different structures against human esophageal cancer cells.
PubMed:Carboxymethylated cyclosophoraose as a novel chiral additive for the stereoisomeric separation of some flavonoids by capillary electrophoresis.
PubMed:Enzymatic conversion of diacetylated sophoroselipid into acetylated glucoselipid: surface-active properties of novel bolaform biosurfactants.
PubMed:Efficient chemoenzymatic oligosaccharide synthesis by reverse phosphorolysis using cellobiose phosphorylase and cellodextrin phosphorylase from Clostridium thermocellum.
PubMed:13C-metabolic flux ratio and novel carbon path analyses confirmed that Trichoderma reesei uses primarily the respirative pathway also on the preferred carbon source glucose.
PubMed:Panose, a new prebiotic candidate.
PubMed:Identification of free disaccharides and other glycosides in wine.
PubMed:Functional new acylated sophoroses and deglucosylated anthocyanins in a fermented red vinegar.
PubMed:Structural analysis of three novel trisaccharides isolated from the fermented beverage of plant extracts.
PubMed:Knocking out the MFE-2 gene of Candida bombicola leads to improved medium-chain sophorolipid production.
PubMed:The neurite-initiating effect of microbial extracellular glycolipids in PC12 cells.
PubMed:Novel family of carbohydrate esterases, based on identification of the Hypocrea jecorina acetyl esterase gene.
PubMed:Lactose enhances cellulase production by the filamentous fungus Acremonium cellulolyticus.
PubMed:Identification of the cis-acting elements involved in regulation of xylanase III gene expression in Trichoderma reesei PC-3-7.
PubMed:Enzymatic properties of cellobiose 2-epimerase from Ruminococcus albus and the synthesis of rare oligosaccharides by the enzyme.
PubMed:Conformational analysis of beta-glycosidic linkages in 13C-labeled glucobiosides using inter-residue scalar coupling constants.
PubMed:Characterization of a thermostable extracellular beta-glucosidase with activities of exoglucanase and transglycosylation from Paecilomyces thermophila.
PubMed:Enzymatic characterization and substrate specificity of thermostable beta-glycosidase from hyperthermophilic archaea, Sulfolobus shibatae, expressed in E. coli.
PubMed:Screening and characterization of an enzyme with beta-glucosidase activity from environmental DNA.
PubMed:Purification and biochemical characterization of an extracellular beta-glucosidase from the wood-decaying fungus Daldinia eschscholzii (Ehrenb.:Fr.) Rehm.
PubMed:Vibrational circular dichroism (VCD) studies on disaccharides in the CH region: toward discrimination of the glycosidic linkage position.
PubMed:Molecular cloning and transcriptional expression analysis of an intracellular beta-glucosidase, a family 3 glycosyl hydrolase, from the edible straw mushroom, Volvariella volvacea.
PubMed:Purification by silica gel chromatography using dialysis tubing and characterization of sophorolipids produced from Candida bombicola grown on glucose and arachidonic acid.
PubMed:Xyr1 (xylanase regulator 1) regulates both the hydrolytic enzyme system and D-xylose metabolism in Hypocrea jecorina.
PubMed:Construction and characterization of chimeric enzymes of kojibiose phosphorylase and trehalose phosphorylase from Thermoanaerobacter brockii.
PubMed:Conformational and dynamical properties of disaccharides in water: a molecular dynamics study.
PubMed:The use of fatty acid esters to enhance free acid sophorolipid synthesis.
PubMed:Induction of Mannanase, Xylanase, and Endoglucanase Activities in Sclerotium rolfsii.
PubMed:Family 3 beta-glucosidase from cellulose-degrading culture of the white-rot fungus Phanerochaete chrysosporium is a glucan 1,3-beta-glucosidase.
PubMed:Transfer of high-mannose-type oligosaccharides to disaccharides by endo-beta-N-acetylglucosaminidase from Arthrobacter protophormiae.
PubMed:Induction and catabolite repression mechanisms of cellulase in fungi.
PubMed:Substrate specificity and transglycosylation catalyzed by a thermostable beta-glucosidase from marine hyperthermophile Thermotoga neapolitana.
PubMed:Influence of disaccharide structure on prebiotic selectivity in vitro.
PubMed:ooc1, a unique gene expressed only during growth of Hypocrea jecorina (anamorph: Trichoderma reesei) on cellulose.
PubMed:A role for the carbohydrate portion of ginsenoside Rg3 in Na+ channel inhibition.
PubMed:Purification and characterization of recombinant Escherichia coli-expressed Pichia etchellsii beta-glucosidase II with high hydrolytic activity on sophorose.
PubMed:Identification and quantification of phenolic compounds in berries of Fragaria and Rubus species (family Rosaceae).
PubMed:Cloning of genes expressed early during cellulase induction in Hypocrea jecorina by a rapid subtraction hybridization approach.
PubMed:LC/MS analysis and lipase modification of the sophorolipids produced by Rhodotorula bogoriensis.
PubMed:Total synthesis of quercetin 3-sophorotrioside.
PubMed:Synthesis and characterization of carboxymethylated cyclosophoraose, and its inclusion complexation behavior.
PubMed:The galactokinase of Hypocrea jecorina is essential for cellulase induction by lactose but dispensable for growth on d-galactose.
PubMed:Nucleosome transactions on the Hypocrea jecorina (Trichoderma reesei) cellulase promoter cbh2 associated with cellulase induction.
PubMed:Regioselective enzyme-catalyzed synthesis of sophorolipid esters, amides, and multifunctional monomers.
PubMed:The effect of medium composition on the structure and physical state of sophorolipids produced by Candida bombicola ATCC 22214.
PubMed:Transcriptional regulation of xyn2 in Hypocrea jecorina.
PubMed:ACEI of Trichoderma reesei is a repressor of cellulase and xylanase expression.
PubMed:Biosynthetic activity of recombinant Escherichia coli-expressed Pichia etchellsii beta-glucosidase II.
PubMed:Enzymatic properties and intracellular localization of the novel Trichoderma reesei beta-glucosidase BGLII (cel1A).
PubMed:Structural basis for broad substrate specificity in higher plant beta-D-glucan glucohydrolases.
PubMed:Oxygen transfer rate and sophorose lipid production by Candida bombicola.
PubMed:[Isolation and properties of cellobiase from Penicillium verruculosum].
PubMed:Enzyme-Mediated Regioselective Acylations of Sophorolipids.
PubMed:The Hypocrea jecorina HAP 2/3/5 protein complex binds to the inverted CCAAT-box (ATTGG) within the cbh2 (cellobiohydrolase II-gene) activating element.
PubMed:Purification and characterization of a beta-glucosidase from Citrus sinensis var. Valencia fruit tissue.
PubMed:Cellobiose uptake in the hyperthermophilic archaeon Pyrococcus furiosus is mediated by an inducible, high-affinity ABC transporter.
PubMed:Purification and characterization of ginsenoside Rb1-metabolizing beta-glucosidase from Fusobacterium K-60, a human intestinal anaerobic bacterium.
PubMed:ACEII, a novel transcriptional activator involved in regulation of cellulase and xylanase genes of Trichoderma reesei.
PubMed:L-Sorbose induces cellulase gene transcription in the cellulolytic fungus Trichoderma reesei.
PubMed:Influence of exogenous natural oils on the omega-1 and omega-2 hydroxy fatty acid moiety of sophorose lipid produced by Candida bombicola.
PubMed:Cloning and biochemical characterization of BglC, a beta-glucosidase from the cellulolytic actinomycete Thermobifida fusca.
PubMed:Constitutive beta-glucosidases hydrolyzing ginsenoside Rb1 and Rb2 from human intestinal bacteria.
PubMed:Regulation of xyn3 gene expression in Trichoderma reesei PC-3-7.
PubMed:Molecular dynamics simulations of cyclohenicosakis-[(1-->2)-beta-D-gluco-henicosapyranosyl], a cyclic (1-->2)-beta-D-glucan (a 'cyclosophoraose') of DP 21.
PubMed:Purification and some properties of a beta-glucosidase from Flavobacterium johnsonae.
PubMed:Ring-closing alkyne metathesis. Application to the total synthesis of sophorolipid lactone.
PubMed:Two cellobiohydrolase-encoding genes from Aspergillus niger require D-xylose and the xylanolytic transcriptional activator XlnR for their expression.
PubMed:The protein disulphide isomerase gene of the fungus Trichoderma reesei is induced by endoplasmic reticulum stress and regulated by the carbon source.
PubMed:Production of sophorolipids from whey: development of a two-stage process with Cryptococcus curvatus ATCC 20509 and Candida bombicola ATCC 22214 using deproteinized whey concentrates as substrates.
PubMed:Wastepaper hydrolysate as soluble inducing substrate for cellulase production in continuous culture of trichoderma reesei
PubMed:Two adjacent protein binding motifs in the cbh2 (cellobiohydrolase II-encoding) promoter of the fungus Hypocrea jecorina (Trichoderma reesei) cooperate in the induction by cellulose.
PubMed:Role of four major cellulases in triggering of cellulase gene expression by cellulose in Trichoderma reesei.
PubMed:Purification and characterization of an extracellular beta-glucosidase from the filamentous fungus Acremonium persicinum and its probable role in beta-glucan degradation.
PubMed:Effect of soybean oil and glucose on sophorose lipid fermentation by Torulopsis bombicola in continuous culture.
PubMed:Cellulase induction in Trichoderma reesei by cellulose requires its own basal expression.
PubMed:Microbial extracellular glycolipid induction of differentiation and inhibition of the protein kinase C activity of human promyelocytic leukemia cell line HL60.
PubMed:Regulation of cellulase gene expression in the filamentous fungus Trichoderma reesei.
PubMed:Phospho-beta-glucosidase from Fusobacterium mortiferum: purification, cloning, and inactivation by 6-phosphoglucono-delta-lactone.
PubMed:Functional analysis of the cellobiohydrolase I promoter of the filamentous fungus Trichoderma reesei.
PubMed:Purification and Characterization of an Extracellular beta-Glucosidase from the Wood-Grown Fungus Xylaria regalis
PubMed:Different inducibility of expression of the two xylanase genes xyn1 and xyn2 in Trichoderma reesei.
PubMed:Mutants of Trichoderma reesei are defective in cellulose induction, but not basal expression of cellulase-encoding genes.
PubMed:Initial steps of sophoroselipid biosynthesis by Candida bombicola ATCC 22214 grown on glucose.
PubMed:Transcriptional control of the cellulase genes in Trichoderma reesei.
PubMed:Enhanced Expression of Endochitinase in Trichoderma harzianum with the cbh1 Promoter of Trichoderma reesei.
PubMed:Cytochromes P450 of the sophorose lipid-producing yeast Candida apicola: heterogeneity and polymerase chain reaction-mediated cloning of two genes.
PubMed:Endoglucanase II (EGII) of Penicillium janthinellum: cDNA sequence, heterologous expression and promotor analysis.
PubMed:Isolation and characterization of an enzyme with beta-glucosidase and beta-fucosidase activities from Dalbergia cochinchinensis Pierre.
PubMed:The bgl1 gene of Trichoderma reesei QM 9414 encodes an extracellular, cellulose-inducible beta-glucosidase involved in cellulase induction by sophorose.
PubMed:Nor-cucurbitacin glucosides from Caputo nigri.
PubMed:Flavonoids from Iochroma gesnerioides.
PubMed:Petite mutants of sophorolipid-producing Candida yeasts.
PubMed:Isolation and properties of an extracellular beta-glucosidase from the polycentric rumen fungus Orpinomyces sp. strain PC-2.
PubMed:Improved chromatographic purification of peroxidase and beta-glucosidase from Hordeum vulgare seedlings.
PubMed:Triggering of cellulase biosynthesis by cellulose in Trichoderma reesei. Involvement of a constitutive, sophorose-inducible, glucose-inhibited beta-diglucoside permease.
PubMed:Metabolic regulation of endoglucanase synthesis in Trichoderma reesei: participation of cyclic AMP and glucose-6-phosphate.
PubMed:Thermostable beta-glucosidase and beta-xylosidase from Thermotoga sp. strain FjSS3-B.1.
PubMed:Characterization of the Trichoderma reesei cbh2 promoter.
PubMed:The bgl1 gene encoding extracellular beta-glucosidase from Trichoderma reesei is required for rapid induction of the cellulase complex.
PubMed:Conformational analysis of the anomeric forms of sophorose, laminarabiose, and cellobiose using MM3.
PubMed:Synthesis of four novel trisaccharides by induction of loose acceptor specificity in Gal beta 1----4 transferase (EC 2.4.1.22): Galp(beta 1----4)Glcp(X)Glc where X = beta 1----3: beta 1----4: beta 1----6: alpha 1----4.
PubMed:Linkage analysis in disaccharides by electrospray mass spectrometry.
PubMed:Induction of cellulose- and xylan-degrading enzyme systems in Aspergillus terreus by homo- and heterodisaccharides composed of glucose and xylose.
PubMed:1H-nuclear magnetic resonance spectroscopy of reducing-residue anomeric protons of pertrifluoroacetylated carbohydrates.
PubMed:Purification and properties of two lactose hydrolases from Trichosporon cutaneum.
PubMed:Biotransformation of digitoxigenin by ginseng hairy root cultures.
PubMed:Effect of the addition of microbial surfactants on hydrocarbon degradation in a soil population in a stirred reactor.
PubMed:Mechanism by which cellulose triggers cellobiohydrolase I gene expression in Trichoderma reesei.
PubMed:A cell-associated oligo-1,6-alpha-glucosidase from an extremely thermophilic anaerobic bacterium, Thermoanaerobium Tok6-B1.
PubMed:Differential regulation of synthesis of multiple forms of specific endoglucanases by Trichoderma reesei QM9414.
PubMed:Stability and substrate specificity of a beta-glucosidase from the thermophilic bacterium Tp8 cloned into Escherichia coli.
PubMed:Involvement of a conidial endoglucanase and a plasma-membrane-bound beta-glucosidase in the induction of endoglucanase synthesis by cellulose in Trichoderma reesei.
PubMed:[Toxicological studies on sophorolipid derivatives. (II). Subacute toxicity study of polyoxypropylene (12) [2'-0-beta-D-glucopyranosyl-beta-D-glucopyranosyl) oxy-] fatty acid ester-].
PubMed:[Toxicological studies on sophorolipid derivatives. (I). Acute toxicity, eye irritation, primary skin irritation, skin sensitization, phototoxicity, photosensitization, mutagenicity of polyoxypropylene (12) [(2'-0-beta-D-glucopyranosyl-beta-D-glucopyranosyl)oxy-] fatty acid ester-].
PubMed:The enzymatic synthesis of beta 1-2 glucans.
PubMed:Biosynthesis of membrane-derived oligosaccharides. Novel glucosyltransferase system from Escherichia coli for the elongation of beta 1----2-linked polyglucose chains.
PubMed:Sophorose induction of an intracellular b-glucosidase in Trichoderma.
PubMed:Identification of the major antigenic determinants on lipoglycans from Acholeplasma granularum and Acholeplasma axanthum.
PubMed:Repression of endo-1,4-beta-glucanase formation in Penicillium janthinellum and product inhibition of its 1,4-beta-glucanases and cellobiases.
PubMed:Induction of cellulose in Schizophyllum commune: thiocellobiose as a new inducer.
PubMed:Regulatory controls in relation to over-production of fungal cellulases.
PubMed:Regulation of the cellulolytic system in Trichoderma reesei by sophorose: induction of cellulase and repression of beta-glucosidase.
PubMed:Partial purification and characterization of a new intracellular beta-glucosidase of Trichoderma reesei.
PubMed:Induction of cellulolytic enzymes in Trichoderma reesei by sophorose.
PubMed:Surface carbohydrates of Rhizobium. I. Beta-1, 2-glucans.
PubMed:Cellulase and beta-glucosidase production by a basidiomycete species.
PubMed:Sophorose metabolism and cellulase induction in Trichoderma.
PubMed:Induction of D-aldohexoside:cytochrome c oxidoreductase in Agrobacterium tumefaciens.
PubMed:Derepressed synthesis of cellulase by Cellulomonas.
PubMed:Characterization and in vivo production of three glycolipids from Candida Bogoriensis: 13-glucopyranosylglucopyranosyloxydocosanoic acid and its mono- and diacetylated derivatives.
PubMed:Inductive formation of cellulase by sophorose in Trichoderma viride.
PubMed:"De novo" synthesis of cellulase' induced by sophorose in Trichoderma viride cells.
PubMed:Some biological properties of Pneumococcus type 37 and the chemistry of its capsular polysaccharide.
PubMed:Protein-carbohydrate interaction. XX. The interaction of concanavalin A with sophorose and some of its derivatives.
PubMed:Sophorose as an inducer of cellulase in Trichoderma viride.
PubMed:Formation of gentiobiose, sophorose and other oligosaccharides by Acetobacter species growing in glucose media.
PubMed:Detection of gentiobiose and sophorose in cultures of certain micro-organisms growing in defined glucose-containing media.
 
Notes:
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