367-93-1

Basic information

• Product Name: Isopropyl-beta-D-thiogalactopyranoside
• Synonyms: POLYETYLENE GLYCOL 6000 MOL. BIOLOGY GRA;SULPHURIC ACID 0,01 MOL/L 0,02 N;YPD BROTH E;Isopropyl 2,3-O-isopropylidene-4-O-benzoyl-β-L-thiorhamnopyranoside;IPTG (Isopropyl-β-D-thiogalatopyranoside);Isopropyl-beta-D-thiogalactopyranoside, ;Isopropyl-beta-D-thiogalactopyranoside, ;Isopropyl-beta-D-thiogalactopyranoside, 98.0%+,
• CAS NO: 367-93-1
• Molecular Formula: C₉H₁₈O₅S
• Molecular Weight: 238.3
• EINECS: 206-703-0
• Product Categories: Imidazolines/Imidazolidines ,Imidazoles ,Heterocyclic Acids;Substrates;13C & 2H Sugars;Biochemistry;Galactose;Glycosides;Sugars;Thioglycosides;Enzyme substrates;Carbohydrates & Derivatives;Carbohydrates;substrate
• Mol File: 367-93-1.mol

Chemical Properties

• Melting Point: 105 °C
• Boiling Point: 350.9°C (rough estimate)
• Flash Point: 219 ºC
• Appearance: White/Crystalline Powder
• Density: 1.3329 (rough estimate)
• Vapor Pressure: 1.58E-09mmHg at 25°C
• Refractive Index: 1.5060 (estimate)
• Storage Temp.: −20°C
• Solubility: Soluble in Water or Methanol.
• PKA: 13.00±0.70(Predicted)
• Water Solubility: soluble
• Stability: Stable. Incompatible with strong oxidizing agents.
• Merck: 14,5082
• BRN: 4631
• CAS DataBase Reference: Isopropyl-beta-D-thiogalactopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: Isopropyl-beta-D-thiogalactopyranoside(367-93-1)
• EPA Substance Registry System: Isopropyl-beta-D-thiogalactopyranoside(367-93-1)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 19-40-66-36/37/38
• Safety Statements: 23-24/25-36/37-22-36/37/39-27-26
• WGK Germany: 3
• F: 10
• TSCA: Yes
• Hazardous Substances Data: 367-93-1(Hazardous Substances Data)

Usage

Chemical Properties

White crystalline powder

Uses

Isopropyl-β-D-thiogalactoside is used as a reagent in molecular biology. It is used as an effective β-galactosidase inducer of protein expression where the gene is under the control of the lac operator. It is used with 5-bromo-4-chloro-3-indolyl-beta-D-galactopyranoside to identify the non-recombinant plasmid in cloning experiments by blue-white screen methodology.

Definition

ChEBI: Isopropyl beta-D-thiogalactopyranoside is an S-glycosyl compound consisting of beta-D-1-thiogalactose having an isopropyl group attached to the anomeric sulfur.

Application

IPTG (Isopropyl-β-D-thiogalactopyranoside) is a galactose analogue not recognized by β-galactosidase. IPTG is a non-metabolizable galactose analog that induces expression of the lac operon in Escherichia coli. It is a commonly used reagent in cloning procedures that require induction of b-galactosidase activity and is used in conjunction with X-Gal. It is commonly used in cloning procedures that require induction of β-galactosidase activity. It is also used in conjunction with X-Gal or Bluo-Gal in blue-white selection of recombinant bacterial colonies that induce expression of the lac operon in Escherichia coli. IPTG functions by binding to the lacI repressor and altering its conformation, which prevents the repression of the β-galactosidase coding gene lacZ.

Preparation

a synthetic method of isopropyl-β-D-thiogalactoside. The steps are as follows:Step 1: Dissolve β-D-galactose pentaacetate in any organic solvent of methylene chloride, chloroform or 1,2-dichloroethane, and add Lewis acid (boron trifluoride ether, (Aluminum trichloride, zinc chloride) catalyst and potassium ethylxanthate or sodium ethylxanthate are reacted to obtain tetraacetylgalactose ethylxanthate after treatment.Step 2: Dissolve tetraacetyl galactose ethyl xanthate, 2-bromopropane and sodium carbonate in methanol or ethanol at a temperature of 20°C to 80°C and react for 4-6 hours to obtain isopropyl group after treatment Isopropyl-β-D-thiogalactoside.

General Description

Inducer for β-galactosidase, an enzyme that promotes lactose utilization. Use in conjunction with X-Gal. Molecular Biology grade.Stock solutions:X-Gal: 20 mg/ml in DMFIPTG: 20 mg/ml in waterUse 4:1 (X-Gal:IPTG)Assay: ≥99%Dioxane: None detectedMelting point: 110-114°CSpecific rotation [a]25/D (1%, water): -34.0 to -29.0° Intended for laboratory and manufacturing use only. Not for drug, food, or household use.

storage

Store powder at -20°C away from direct sunlight. Once opened and recapped, place container in a low humidity environment at the same storage temperature. Protect from moisture and light by keeping container tightly closed.

InChI:InChI=1/C9H18O5S/c1-4(2)15-9-8(13)7(12)6(11)5(3-10)14-9/h4-13H,3H2,1-2H3/t5-,6+,7+,8-,9?/m1/s1

Synthetic route

isopropyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopiranoside (55692-87-0) → isopropyl β-D-thiogalactopyranoside (367-93-1)

Conditions	Yield
With sodium methylate In methanol at 20℃; pH=10;	98%
With sodium methylate In methanol for 0.5h;	90%
With sodium methylate In methanol at 20℃; for 5h; pH=10;	81%

2,3,4,6-Tetra-O-acetyl-β-D-galactopyranosyl-aethylxanthat (29587-08-4) + isopropyl bromide (75-26-3) → isopropyl β-D-thiogalactopyranoside (367-93-1)

Conditions	Yield
With methanol; potassium carbonate at 60℃; for 5h; Reagent/catalyst; Temperature;	92%

isopropylthio-6-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)carbonate)-β-D-galactopyranoside → isopropyl β-D-thiogalactopyranoside (367-93-1)

Conditions	Yield
With sodium L-ascorbate; fluorescein free acid In aq. phosphate buffer for 0.5h; pH=7.4; Irradiation;	75%

D-Galactose (10257-28-0) + 2-propanethiol (75-33-2) → isopropyl β-D-thiogalactopyranoside (367-93-1)

Conditions	Yield
Stage #1: D-Galactose; 2-propanethiol With aluminum (III) chloride; acetic anhydride at 5 - 10℃; Stage #2: With sodium methylate In methanol Reagent/catalyst;	74.3%

D-galactose pentaacetate (25878-60-8) + 2-propanethiol (75-33-2) → isopropyl β-D-thiogalactopyranoside (367-93-1)

Conditions	Yield
Stage #1: D-galactose pentaacetate; 2-propanethiol With boron trifluoride diethyl etherate In dichloromethane at 0 - 5℃; for 2h; Stage #2: With sodium methylate In methanol	45.2%

2-propanethiol (75-33-2) + β-D-galactose peracetate (4163-60-4) → isopropyl β-D-thiogalactopyranoside (367-93-1)

Conditions	Yield
Stage #1: 2-propanethiol; β-D-galactose peracetate With boron trifluoride diethyl etherate In dichloromethane at 0 - 5℃; for 2h; Stage #2: With sodium methylate In methanol	45.2%

2-propanethiol (75-33-2) + 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside (3068-32-4) → isopropyl β-D-thiogalactopyranoside (367-93-1)

Conditions	Yield
With potassium ethoxide Behandeln des Reaktionsprodukts mit Natriummethylat in Methanol;

β-D-galactose peracetate (4163-60-4) → isopropyl β-D-thiogalactopyranoside (367-93-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 75 percent / BF3*Et2O / CH2Cl2 / 1.5 h / 20 °C 2: 81 percent / CH3ONa / methanol / 5 h / 20 °C / pH 10 View Scheme
Multi-step reaction with 4 steps 1: thiourea; boron trifluoride diethyl etherate / dichloromethane / 12 h / 20 °C 2: sodium metabisulfite / dichloromethane; water / Reflux 3: potassium carbonate / acetone / 20 °C 4: sodium methylate / methanol / 20 °C / pH 10 View Scheme

2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl fluoride (439-03-2, 439-04-3, 439-05-4, 2823-44-1, 2823-46-3, 3934-29-0, 4163-45-5, 20409-31-8, 23235-96-3, 51897-75-7, 51897-76-8, 51897-77-9, 57573-38-3, 62561-28-8, 126641-47-2, 4163-44-4) → isopropyl β-D-thiogalactopyranoside (367-93-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: BF3*OEt2 / CH2Cl2 / 0.17 h / Ambient temperature 2: 72 percent / NaOMe / methanol / 1 h / Ambient temperature View Scheme

2,3,4,6-tetra-O-acetyl-α/β-D-galactopyranose (3947-62-4, 6207-76-7, 10343-06-3, 19235-21-3, 22554-70-7, 22860-22-6, 57884-82-9, 62057-79-8, 70191-05-8, 109525-54-4, 140147-37-1, 47339-09-3) → isopropyl β-D-thiogalactopyranoside (367-93-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1) NaH, Molekularsieb 4 A, 2) 0.1 M BF3*OEt2, Molekularsieb 4 A / 1) CH2Cl2, 30 min, RT, 2) CH2Cl2, 30 min, RT 2: 90 percent / 0.5 M CH3ONa / methanol / 0.5 h View Scheme

β-D-galactopyranoside (7296-64-2) + 2-propanethiol (75-33-2) → isopropyl β-D-thiogalactopyranoside (367-93-1)

Conditions	Yield
With potassium acetate In acetic anhydride at 80℃;	0.5 kg

D-Galactose (59-23-4) → isopropyl β-D-thiogalactopyranoside (367-93-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: zinc(II) chloride / 0.2 h / 5 - 10 °C 2: sodium methylate / methanol View Scheme
Multi-step reaction with 3 steps 1: sodium acetate / 0.2 h / Reflux 2: boron trifluoride diethyl etherate / dichloromethane / 2 h / 0 - 5 °C 3: sodium methylate / methanol View Scheme

S-tetraacetyl-β-D-galactosylisothiourea fluorine salt → isopropyl β-D-thiogalactopyranoside (367-93-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium metabisulfite / dichloromethane; water / Reflux 2: potassium carbonate / acetone / 20 °C 3: sodium methylate / methanol / 20 °C / pH 10 View Scheme

BEC-cIPTG → C15H17NO10 + isopropyl β-D-thiogalactopyranoside (367-93-1)

Conditions	Yield
Stage #1: BEC-cIPTG UV-irradiation; Stage #2: With water Enzymatic reaction;

BEC-cIPTG → C11H7NO10(2-)*2Li(1+) + isopropyl β-D-thiogalactopyranoside (367-93-1)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: lithium hydroxide; water / methanol / 1 h / 0 - 20 °C 2.1: UV-irradiation 2.2: Enzymatic reaction View Scheme

BC-cIPTG → C11H7NO10(2-)*2Li(1+) + isopropyl β-D-thiogalactopyranoside (367-93-1)

Conditions	Yield
Stage #1: BC-cIPTG UV-irradiation; Stage #2: With water Enzymatic reaction;

acetic anhydride (108-24-7) + isopropyl β-D-thiogalactopyranoside (367-93-1) → isopropyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopiranoside (55692-87-0)

Conditions	Yield
With pyridine	100%
With pyridine at 20℃;	100%

benzaldehyde dimethyl acetal (1125-88-8) + isopropyl β-D-thiogalactopyranoside (367-93-1) → isopropyl 4,6-di-O-benzylidene-1-thio-β-D-galactopyranoside

Conditions	Yield
toluene-4-sulfonic acid In dichloromethane at 20℃; for 2h;	96%
With camphor-10-sulfonic acid In N,N-dimethyl-formamide at 0 - 20℃;	82%
With camphor-10-sulfonic acid In N,N-dimethyl-formamide at 20℃; pH=2 - 3;	82%

isopropyl β-D-thiogalactopyranoside (367-93-1) + p-methoxybenzyl chloride (824-94-2) → C41H50O9S

Conditions	Yield
Stage #1: isopropyl β-D-thiogalactopyranoside With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5h; Schlenk technique; Inert atmosphere; Stage #2: p-methoxybenzyl chloride In N,N-dimethyl-formamide; mineral oil at 23℃; for 17h; Schlenk technique; Inert atmosphere;	95%

isopropyl β-D-thiogalactopyranoside (367-93-1) + tert-butyldimethylsilyl chloride (18162-48-6) → isopropyl 1-thio-6-O-(tert-butyldimethylsilyl)-β-D-galactopyranoside (1273157-53-1)

Conditions	Yield
With triethylamine; N,N-dimethyl-formamide In acetonitrile at 20℃; for 0.5h; regioselective reaction;	92%
With pyridine at 0 - 20℃; for 14h; Inert atmosphere;	88.1%
With pyridine at 23℃;	84%
With pyridine at 20℃; for 16h;

isopropyl β-D-thiogalactopyranoside (367-93-1) + 4-Nitrobenzenesulfonyl chloride (98-74-8) → isopropylthio 3-O-(4-nitrobenzenesulfonyl)-β-D-galactopyranoside

Conditions	Yield
With 2-((S)-quinolin-4-yl((1S,2S,4S,5R)-5-vinylquinuclidin-2-yl)methyl)-2,3-dihydro-1H-benzo[c][1,2]azaborol-1-ol; sodium carbonate In acetonitrile at 20℃; for 20h; regioselective reaction;	88%

benzyl bromide (100-39-0) + isopropyl β-D-thiogalactopyranoside (367-93-1) → isopropyl 2,3,4,6-tetra-O-benzyl-1-thio-α-D-galactopyranoside (440652-81-3)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 20℃; for 6h;	85%

isopropyl β-D-thiogalactopyranoside (367-93-1) + benzoyl chloride (98-88-4) → isopropyl 2,3,4,6-tetra-O-benzoyl-1-thio-β-D-galactopyranoside

Conditions	Yield
With pyridine; dmap at 20℃; Concentration;	85%

isopropyl β-D-thiogalactopyranoside (367-93-1) + p-toluenesulfonyl chloride (98-59-9) → isopropylthio 3-O-(4-toluenesulfonyl)-β-D-galactopyranoside

Conditions	Yield
With 1-methyl-1H-imidazole; 2-((S)-quinolin-4-yl((1S,2S,4S,5R)-5-vinylquinuclidin-2-yl)methyl)-2,3-dihydro-1H-benzo[c][1,2]azaborol-1-ol; sodium carbonate In acetonitrile at 20℃; for 18h; regioselective reaction;	84%

3,5-bis(trifluoromethyl)benzenesulfonyl chloride (39234-86-1) + isopropyl β-D-thiogalactopyranoside (367-93-1) → isopropylthio 3-O-(3,5-bis(trifluoromethyl)benzenesulfonyl)-β-D-galactopyranoside

Conditions	Yield
With 2-((S)-quinolin-4-yl((1S,2S,4S,5R)-5-vinylquinuclidin-2-yl)methyl)-2,3-dihydro-1H-benzo[c][1,2]azaborol-1-ol; sodium carbonate In acetonitrile at 20℃; for 20h; regioselective reaction;	82%

isopropyl β-D-thiogalactopyranoside (367-93-1) + allyl bromide (106-95-6) → (2R,3S,4S,5R,6S)-4-Allyloxy-2-hydroxymethyl-6-isopropylsulfanyl-tetrahydro-pyran-3,5-diol (847225-60-9)

Conditions	Yield
Stage #1: isopropyl β-D-thiogalactopyranoside In methanol for 2h; Heating; Stage #2: allyl bromide With tetra-(n-butyl)ammonium iodide In toluene at 60℃; for 24h;	79%

benzaldehyde dimethyl acetal (1125-88-8) + isopropyl β-D-thiogalactopyranoside (367-93-1) → C16H22O5S (936549-98-3)

Conditions	Yield
With toluene-4-sulfonic acid In dichloromethane; water for 2h;	79%

6-nitro-1,3-benzodioxole-5-carbaldehyde (712-97-0) + isopropyl β-D-thiogalactopyranoside (367-93-1) → NP-cIPTG

Conditions	Yield
With sulfuric acid In dimethyl sulfoxide at 0 - 20℃;	78%
With sulfuric acid In dimethyl sulfoxide at 0 - 20℃; for 24h;	21%

benzyl bromide (100-39-0) + isopropyl β-D-thiogalactopyranoside (367-93-1) → isopropyl 3-O-benzyl-1-thio-β-D-galactopyranoside

Conditions	Yield
Stage #1: isopropyl β-D-thiogalactopyranoside With di(n-butyl)tin oxide In methanol; toluene for 4h; Reflux; Stage #2: benzyl bromide With tetrabutylammomium bromide In toluene at 70℃; for 5h; regioselective reaction;	78%

isopropyl β-D-thiogalactopyranoside (367-93-1) + benzoyl chloride (98-88-4) → 3,6-di-O-benzoylated-isopropyl-β-D-1-thiogalactopyranoside (615570-19-9)

Conditions	Yield
With pyridine at -10℃;	70%
With pyridine at 0℃; Concentration;	0.98 g

N-benzoyloxybenzotriazole (54769-36-7) + isopropyl β-D-thiogalactopyranoside (367-93-1) → 3,6-di-O-benzoylated-isopropyl-β-D-1-thiogalactopyranoside (615570-19-9)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 10h; regioselective reaction;	69%

isopropyl β-D-thiogalactopyranoside (367-93-1) + N-ethyl-N,N-diisopropylamine (7087-68-5) → C9H18O8S2*C8H19N + C9H18O11S3*2C8H19N

Conditions	Yield
With sulfur trioxide trimethylamine complex; 10-hydroxy-4a,10a-dihydrobenzo[b][1,4]benzoxaborinine In acetonitrile at 60℃; for 3h; Inert atmosphere;	A 69% B 24%

tert-butyl (1-phenylprop-2-yn-1-yl) carbonate + isopropyl β-D-thiogalactopyranoside (367-93-1) → (2S,3R,4S,5R,6R)-2-(isopropylthio)-6-((((R)-1-phenylprop-2-yn-1-yl)oxy)methyl)tetrahydro-2H-pyran-3,4,5-triol + (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(isopropylthio)-4-(((S)-1-phenylprop-2-yn-1-yl)oxy)tetrahydro-2H-pyran-3,5-diol

Conditions	Yield
With tetrakis(acetonitrile)copper(I)tetrafluoroborate; R,R-C5H3N(C3H3NOPh)2; triethylamine; 10-hydroxy-4a,10a-dihydrobenzo[b][1,4]benzoxaborinine In tetrahydrofuran Molecular sieve; Inert atmosphere; Sealed tube;	A n/a B 66%

tert-butyl (1-phenylprop-2-yn-1-yl) carbonate + isopropyl β-D-thiogalactopyranoside (367-93-1) → (2S,3R,4S,5R,6R)-2-(isopropylthio)-6-((((R)-1-phenylprop-2-yn-1-yl)oxy)methyl)tetrahydro-2H-pyran-3,4,5-triol

Conditions	Yield
With 2,6-bis[(4S)-4-methyl-4,5-dihydrooxazol-2-yl]pyridine; tetrakis(acetonitrile)copper(I)tetrafluoroborate; triethylamine; 10-hydroxy-4a,10a-dihydrobenzo[b][1,4]benzoxaborinine In tetrahydrofuran at 20℃; for 6h; Molecular sieve; Inert atmosphere; Sealed tube;	65%

isopropyl β-D-thiogalactopyranoside (367-93-1) + 2-trifluoromethylbenzoyl chloride (312-94-7) → 3,5-dihydroxy-2-(hydroxymethyl)-6-(isopropylthio)tetrahydro-2H-pyran-4-yl 2-(trifluoromethyl)benzoate

Conditions	Yield
With 2-((S)-quinolin-4-yl((1S,2S,4S,5R)-5-vinylquinuclidin-2-yl)methyl)-2,3-dihydro-1H-benzo[c][1,2]azaborol-1-ol; sodium carbonate In acetonitrile at 20℃; for 48h; regioselective reaction;	62%

isopropyl β-D-thiogalactopyranoside (367-93-1) + N-ethyl-N,N-diisopropylamine (7087-68-5) → C9H18O8S2*C8H19N + C9H18O8S2*C8H19N + C9H18O11S3*2C8H19N

Conditions	Yield
With sulfur trioxide trimethylamine complex; 10-hydroxy-4a,10a-dihydrobenzo[b][1,4]benzoxaborinine In acetonitrile at 60℃; for 3h; Inert atmosphere;	A 58% B 6% C 18%

4,5-bis(ethoxycarbonylmethoxy)-2-nitrobenzylaldehyde diethyl acetal + isopropyl β-D-thiogalactopyranoside (367-93-1) → BEC-cIPTG

Conditions	Yield
With toluene-4-sulfonic acid In dichloromethane at 20℃; for 20h;	45%

isopropyl β-D-thiogalactopyranoside (367-93-1) + 2,2-dimethoxy-propane (77-76-9) → isopropyl 3,4-O-(1-methylethylidene)-1-thio-β-D-galactopyranoside

Conditions	Yield
With camphor-10-sulfonic acid In acetone at 20℃;	40%
With camphor-10-sulfonic acid In acetonitrile at 20℃; for 1h; Inert atmosphere;

isopropyl β-D-thiogalactopyranoside (367-93-1) + benzoyl chloride (98-88-4) → isopropyl 2,3,6-tri-O-benzoyl-1-thio-β-D-galactopyranoside

Conditions	Yield
With pyridine at -10℃; for 3h;	40%

4,6-dimethoxy-1,3,5-triazin-2-yl α-N-acetylglucosaminide (1337923-38-2) + isopropyl β-D-thiogalactopyranoside (367-93-1) → i-propyl 1-thio-4-O-(2-acetamido-2-deoxy-α-glucopyranosyl)-β-galactopyranoside (1352031-32-3)

Conditions	Yield
With Bacteroides thetaiotaomicron VPI5482 α-N-acetylglucosaminidase B1 at 37℃; for 1h; pH=6.5; aq. phosphate buffer; Enzymatic reaction; regioselective reaction;	29%

Upstream product

• 75-33-2 2-propanethiol 
• 3068-32-4 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside 
• 29587-08-4 2,3,4,6-Tetra-O-acetyl-β-D-galactopyranosyl-aethylxanthat 
• 75-26-3 isopropyl bromide 
• 4163-60-4 β-D-galactose peracetate 
• 25878-60-8 D-galactose pentaacetate 
• 10257-28-0 D-Galactose 
• 59-23-4 D-Galactose 
• 7296-64-2 β-D-galactopyranoside 
• 3947-62-4 2,3,4,6-tetra-O-acetyl-α/β-D-galactopyranose 
• 439-03-2 2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl fluoride 
• 55692-87-0 isopropyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside 

Downstream Products

• 669695-14-1 (2S,3R,4S,5R,6R)-2-Isopropylsulfanyl-6-trityloxymethyl-tetrahydro-pyran-3,4,5-triol 
• 1273157-59-7 isopropylthio 6-O-(tert-butyldimethylsilyloxy)-3-O-benzoyl-β-D-galactopyranoside 
• 936549-98-3 C₁₆H₂₂O₅S 
• 952575-71-2 3-azidopropyl 3-O-benzyl-4,6-O-benzylidene-β-D-galactopyranoside 

Relevant articles and documents

Effect of Photocaged Isopropyl β-d-1-thiogalactopyranoside Solubility on the Light Responsiveness of LacI-controlled Expression Systems in Different Bacteria

Photolabile protecting groups play a significant role in controlling biological functions and cellular processes in living cells and tissues, as light offers high spatiotemporal control, is non-invasive as well as easily tuneable. In the recent past, photo-responsive inducer molecules such as 6-nitropiperonyl-caged IPTG (NP-cIPTG) have been used as optochemical tools for Lac repressor-controlled microbial expression systems. To further expand the applicability of the versatile optochemical on-switch, we have investigated whether the modulation of cIPTG water solubility can improve the light responsiveness of appropriate expression systems in bacteria. To this end, we developed two new cIPTG derivatives with different hydrophobicity and demonstrated both an easy applicability for the light-mediated control of gene expression and a simple transferability of this optochemical toolbox to the biotechnologically relevant bacteria Pseudomonas putida and Bacillus subtilis. Notably, the more water-soluble cIPTG derivative proved to be particularly suitable for light-mediated gene expression in these alternative expression hosts.

One-Pot Relay Glycosylation

A novel one-pot relay glycosylation has been established. The protocol is characterized by the construction of two glycosidic bonds with only one equivalent of triflic anhydride. This method capitalizes on the in situ generated cyclic-thiosulfonium ion as the relay activator, which directly activates the newly formed thioglycoside in one pot. A wide range of substrates are well-accommodated to furnish both linear and branched oligosaccharides. The synthetic utility and advantage of this method have been demonstrated by rapid access to naturally occurring phenylethanoid glycoside kankanoside F and resin glycoside merremoside D.

Photocatalysis Enables Visible-Light Uncaging of Bioactive Molecules in Live Cells

The photo-manipulation of bioactive molecules provides unique advantages due to the high temporal and spatial precision of light. The first visible-light uncaging reaction by photocatalytic deboronative hydroxylation in live cells is now demonstrated. Using Fluorescein and Rhodamine derivatives as photocatalysts and ascorbates as reductants, transient hydrogen peroxides were generated from molecular oxygen to uncage phenol, alcohol, and amine functional groups on bioactive molecules in bacteria and mammalian cells, including neurons. This effective visible-light uncaging reaction enabled the light-inducible protein expression, the photo-manipulation of membrane potentials, and the subcellular-specific photo-release of small molecules.

Isopropyl - β - D thio-galactopyranoside synthetic method (by machine translation)

The present invention provides a kind of isopropyl - β - D thio-galactopyranoside synthetic method, namely the method for synthesis of IPTG. Comprises the following steps: five acetyl galactose as raw materials, with the thiourea reaction to obtain the acetyl S - galactose isothiourea fluoro salt, then with the pyrosulfites reaction to obtain the acetyl S - galactose, with isopropyl bromide reaction, the final deacetyl get the compound goal isopropyl - β - D thio-galactopyranoside. In the whole in the reaction process mainly selects the five acetyl galactose and isopropyl bromide as the raw material, not required to be selected smell, toxic isopropyl mercaptan, effectively avoiding harm to human health and the environment, in addition the invention has simple operation, high yield, purity and the like. Is suitable for industrial production. (by machine translation)

Method for synthesizing isopropyl-beta-D-thiogalactoside (IPTG)

The invention provides a method for synthesizing isopropyl-beta-D-thiogalactoside (IPTG) and belongs to the technical field of organic synthesis. The method comprises the following steps: taking a compound beta-D-galactose pentaacetate as a raw material, and reacting with potassium ethyl xanthate in the presence of a catalyst so as to obtain tetraacetyl galactose ethyl xanthate; reacting with 2-bromopropane under an alkaline condition, so as to obtain the isopropyl-beta-D-thiogalactoside (IPTG). According to the synthetic method, the beta-D-galactose pentaacetate, potassium ethyl xanthate and2-bromopropane are taken as main raw materials, 2-mercaptopropane which is extremely unpleasant in smell, easy to diffuse and high in toxicity used in the original method is replaced, and the harm tothe environment is effectively avoided. The raw materials used in the method disclosed by the invention are readily available, the operating process is simple and convenient, the reaction condition ismild, and the method is safe, controllable and high in yield.

A preparation of isopropyl-β-D-thio-galactopyranoside method (by machine translation)

Field of the invention relates to sugar compounds, in particular relates to a preparation of isopropyl-β-D-thio-galactopyranoside method. By adding acetic anhydride and catalyst at room temperature, by adding galactose, after the completion of reaction, adding heteroploid propanethiol, after the reaction is finished after post-processed to obtain isopropylacrylamides thiophosphoro acetyl galactose. ? The isopropyl thio-acetyl galactose added to the methanol solution, adding sodium methoxide, ? After the reaction is finished adding acetic acid neutralization, after post-processed to obtain isopropyl-β-D-thio-galactopyranoside. The method of the invention by the two-step reaction process for synthesizing isopropyl-β-D-thio-galactopyranoside, the operation is simple, easy availability of raw materials, saving the operation cost and material. (by machine translation)

Isopropyl-β-D-thio-galactopyranoside preparation method (by machine translation)

Field of the invention relates to sugar compounds, in particular relates to a preparation of isopropyl? Β? D? Thio-galactopyranoside method. By adding acetic anhydride and catalyst at room temperature, by adding galactose, after the completion of reaction, adding heteroploid propanethiol, after the reaction is finished after post-processed to obtain isopropylacrylamides thiophosphoro acetyl galactose. The isopropyl thio-acetyl galactose added to the methanol solution, adding sodium methoxide, after the completion of reaction is neutralized by adding acetic acid, after post-processed to obtain isopropylacrylamides? Β? D? Thio-galactopyranoside. The method of the invention by the two-step reaction process for synthesizing isopropylacrylamides? Β? D? Thio-galactopyranoside, the operation is simple, easy availability of raw materials, saving the operation cost and material. (by machine translation)

A isopropyl-β-D-thio-galactopyranoside process for preparing

The invention relates to the field of saccharide compounds, particularly a preparation technique of isopropyl-beta-D-thiogalactoside. The technique comprises the following steps: adding acetic anhydride and a catalyst at room temperature, and adding galactose; after the reaction finishes, adding isopropyl mercaptan; after the reaction finishes, carrying out after-treatment to obtain isopropyl thioacetyl galactose; dissolving the isopropyl thioacetyl galactose in methanol, and adding sodium methoxide; and after the reaction finishes, adding acetic acid for neutralization, and carrying out after-treatment to obtain the isopropyl-beta-D-thiogalactoside. The method synthesizes the isopropyl-beta-D-thiogalactoside by a two-step reaction process, is simple to operate and accessible in raw materials, and saves the operating cost and materials.

Isopropyl-β-D-thio-galactopyranoside process for preparing

The invention relates to the field of sugar compounds, and concretely relates to an isopropyl-beta-D-thiogalactoside preparation technology. The technology comprises the following steps: adding acetic anhydride and a catalyst at room temperature, adding galactose, adding isopropyl mercaptan after the above reaction, and post-processing to obtain isopropyl thioacetylgalactosamine; and adding isopropyl thioacetylgalactosamine into methanol for dissolving, adding sodium methoxide, adding acetic acid after the above reaction to neutralize, and post-processing to obtain isopropyl-beta-D-thiogalactoside. The technology allows isopropyl-beta-D-thiogalactoside to be synthesized through a two-step reaction process, and has the advantages of simple operation, easily available raw materials, and saving of the operation cost and materials.

Preparation of isopropyl-β-D-thio-galactopyranoside method

The invention relates to the field of saccharide compounds, particularly a method for preparing isopropyl-beta-D-thiogalactoside. The method comprises the following steps: adding acetic anhydride and a catalyst at room temperature, and adding galactose; after the reaction finishes, adding isopropyl mercaptan; after the reaction finishes, carrying out after-treatment to obtain isopropyl thioacetyl galactose; dissolving the isopropyl thioacetyl galactose in methanol, and adding sodium methoxide; and after the reaction finishes, adding acetic acid for neutralization, and carrying out after-treatment to obtain the isopropyl-beta-D-thiogalactoside. The method synthesizes the isopropyl-beta-D-thiogalactoside by a two-step reaction process, is simple to operate and accessible in raw materials, and saves the operating cost and materials.