[ CAS No. 7240-90-6 ] {[proInfo.proName]}

Name: 7240-90-6|(2S,3R,4S,5R,6R)-2-((5-Bromo-4-chloro-1H-indol-3-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol|98%
Brand: Ambeed
SKU: A788903
Price: 9.0 USD
Availability: InStock
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Quality Control of [ 7240-90-6 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 7240-90-6 ]

SDS Specification

Alternatived Products of [ 7240-90-6 ]

Product Details of [ 7240-90-6 ]

CAS No. :	7240-90-6	MDL No. :
Formula :	C₁₄H₁₅BrClNO₆	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	OPIFSICVWOWJMJ-AEOCFKNESA-N
M.W :	408.63	Pubchem ID :	65181
Synonyms :	BCIG;5-bromo-4-chloro-3-indolyl-β-D-Galactopyranoside	Chemical Name :	(2S,3R,4S,5R,6R)-2-((5-Bromo-4-chloro-1H-indol-3-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Safety of [ 7240-90-6 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 7240-90-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 7240-90-6 ]

[ 7240-90-6 ] Synthesis Path-Downstream 1~29

Yield	Reaction Conditions	Operation in experiment
		The following medium: Columbia base (46.37 g/l), Alizarin-2-β-D-glucoside (0,05 g/l), Ammoniacal iron citrate (0.05 g/l), 5-Bromo-4-chloro-3-indolyl-β-D-galactoside (0,05 g/l), and

2
[ 7240-90-6 ]
fetuin [ No CAS ]
C₂₅H₃₂BrClN₂O₁₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With trans-sialidase from Trypanosoma cruzi at 25℃; Enzymatic reaction;

Reference： [1]Reyes Martinez, Juana Elizabeth; Sardzik, Robert; Voglmeir, Josef; Flitsch, Sabine L. [RSC Advances, 2013, vol. 3, # 44, p. 21335 - 21338]

3
[ 7240-90-6 ]
[ 29245-44-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: trans-sialidase from Trypanosoma cruzi / 25 °C / pH 7 / Enzymatic reaction 2.1: neuraminidase / Enzymatic reaction 2.2: Enzymatic reaction

Reference： [1]Reyes Martinez, Juana Elizabeth; Sardzik, Robert; Voglmeir, Josef; Flitsch, Sabine L. [RSC Advances, 2013, vol. 3, # 44, p. 21335 - 21338]

4
[ 7240-90-6 ]
C₂₅H₃₃BrClN₃O₁₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sialyl-transferase from Photobacterium damsela / 37 °C / pH 7.5 / Enzymatic reaction 2: 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholin-4-ium; ammonium chloride

Reference： [1]Reyes Martinez, Juana Elizabeth; Sardzik, Robert; Voglmeir, Josef; Flitsch, Sabine L. [RSC Advances, 2013, vol. 3, # 44, p. 21335 - 21338]

5
[ 7240-90-6 ]
C₂₅H₃₀BrClN₂O₁₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: trans-sialidase from Trypanosoma cruzi / 25 °C / pH 7 / Enzymatic reaction 2: 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholin-4-ium; ammonium chloride

Reference： [1]Reyes Martinez, Juana Elizabeth; Sardzik, Robert; Voglmeir, Josef; Flitsch, Sabine L. [RSC Advances, 2013, vol. 3, # 44, p. 21335 - 21338]

6
[ 7240-90-6 ]
[ 3063-71-6 ]
C₂₅H₃₂BrClN₂O₁₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sialyl-transferase from Photobacterium damsela at 37℃; Enzymatic reaction;

Reference： [1]Reyes Martinez, Juana Elizabeth; Sardzik, Robert; Voglmeir, Josef; Flitsch, Sabine L. [RSC Advances, 2013, vol. 3, # 44, p. 21335 - 21338]

7
C₂₅H₃₂BrClN₂O₁₄ [ No CAS ]
[ 7240-90-6 ]
sialic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With neuraminidase Enzymatic reaction;

Reference： [1]Reyes Martinez, Juana Elizabeth; Sardzik, Robert; Voglmeir, Josef; Flitsch, Sabine L. [RSC Advances, 2013, vol. 3, # 44, p. 21335 - 21338]

8
[ 7240-90-6 ]
[ 117887-41-9 ]
[ 59-23-4 ]

Yield	Reaction Conditions	Operation in experiment
	With β-galactosidase Enzymatic reaction;

Reference： [1]Kuan, Seah Ling; Ng, David Y. W.; Wu, Yuzhou; Foertsch, Christina; Barth, Holger; Doroshenko, Mikheil; Koynov, Kaloian; Meier, Christoph; Weil, Tanja [Journal of the American Chemical Society, 2013, vol. 135, # 46, p. 17254 - 17257]

9
[ 125328-77-0 ]
[ 7240-90-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 9 steps 1.1: sodium hydroxide; water / 4 h / Reflux 2.1: pyridine / dichloromethane; acetonitrile / 3.5 h / 45 °C / Inert atmosphere 3.1: sodium hydride / N,N-dimethyl-formamide / 0.75 h / Inert atmosphere; Cooling with ice 3.2: Inert atmosphere 4.1: sodium hydride / 6.5 h / 20 °C / Inert atmosphere 5.1: potassium <i>tert</i>-butylate / diethyl ether / 2 h / 40 - 45 °C / Inert atmosphere 6.1: tetra(n-butyl)ammonium hydrogensulfate; potassium carbonate / water; dichloromethane / 20 °C 7.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; morpholine / tetrahydrofuran / 20 °C 8.1: potassium carbonate; silver(I) acetate / 0.33 h / 90 - 100 °C 9.1: sodium methylate / methanol / 20 °C

Reference： [1]Boettcher, Stephan; Thiem, Joachim [European Journal of Organic Chemistry, 2014, vol. 2014, # 3, p. 564 - 574]

10
[ 3030-19-1 ]
[ 7240-90-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 8 steps 1.1: pyridine / dichloromethane; acetonitrile / 3.5 h / 45 °C / Inert atmosphere 2.1: sodium hydride / N,N-dimethyl-formamide / 0.75 h / Inert atmosphere; Cooling with ice 2.2: Inert atmosphere 3.1: sodium hydride / 6.5 h / 20 °C / Inert atmosphere 4.1: potassium <i>tert</i>-butylate / diethyl ether / 2 h / 40 - 45 °C / Inert atmosphere 5.1: tetra(n-butyl)ammonium hydrogensulfate; potassium carbonate / water; dichloromethane / 20 °C 6.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; morpholine / tetrahydrofuran / 20 °C 7.1: potassium carbonate; silver(I) acetate / 0.33 h / 90 - 100 °C 8.1: sodium methylate / methanol / 20 °C

Reference： [1]Boettcher, Stephan; Thiem, Joachim [European Journal of Organic Chemistry, 2014, vol. 2014, # 3, p. 564 - 574]

11
[ 1447125-28-1 ]
[ 7240-90-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: tetra(n-butyl)ammonium hydrogensulfate; potassium carbonate / water; dichloromethane / 20 °C 2: tetrakis(triphenylphosphine) palladium⁽⁰⁾; morpholine / tetrahydrofuran / 20 °C 3: potassium carbonate; silver(I) acetate / 0.33 h / 90 - 100 °C 4: sodium methylate / methanol / 20 °C

Reference： [1]Boettcher, Stephan; Thiem, Joachim [European Journal of Organic Chemistry, 2014, vol. 2014, # 3, p. 564 - 574]

12
[ 943138-45-2 ]
[ 7240-90-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.75 h / Inert atmosphere; Cooling with ice 1.2: Inert atmosphere 2.1: sodium hydride / 6.5 h / 20 °C / Inert atmosphere 3.1: potassium <i>tert</i>-butylate / diethyl ether / 2 h / 40 - 45 °C / Inert atmosphere 4.1: tetra(n-butyl)ammonium hydrogensulfate; potassium carbonate / water; dichloromethane / 20 °C 5.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; morpholine / tetrahydrofuran / 20 °C 6.1: potassium carbonate; silver(I) acetate / 0.33 h / 90 - 100 °C 7.1: sodium methylate / methanol / 20 °C

Reference： [1]Boettcher, Stephan; Thiem, Joachim [European Journal of Organic Chemistry, 2014, vol. 2014, # 3, p. 564 - 574]

13
[ 1447125-22-5 ]
[ 7240-90-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: sodium hydride / 6.5 h / 20 °C / Inert atmosphere 2: potassium <i>tert</i>-butylate / diethyl ether / 2 h / 40 - 45 °C / Inert atmosphere 3: tetra(n-butyl)ammonium hydrogensulfate; potassium carbonate / water; dichloromethane / 20 °C 4: tetrakis(triphenylphosphine) palladium⁽⁰⁾; morpholine / tetrahydrofuran / 20 °C 5: potassium carbonate; silver(I) acetate / 0.33 h / 90 - 100 °C 6: sodium methylate / methanol / 20 °C

Reference： [1]Boettcher, Stephan; Thiem, Joachim [European Journal of Organic Chemistry, 2014, vol. 2014, # 3, p. 564 - 574]

14
[ 1447125-25-8 ]
[ 7240-90-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: potassium <i>tert</i>-butylate / diethyl ether / 2 h / 40 - 45 °C / Inert atmosphere 2: tetra(n-butyl)ammonium hydrogensulfate; potassium carbonate / water; dichloromethane / 20 °C 3: tetrakis(triphenylphosphine) palladium⁽⁰⁾; morpholine / tetrahydrofuran / 20 °C 4: potassium carbonate; silver(I) acetate / 0.33 h / 90 - 100 °C 5: sodium methylate / methanol / 20 °C

Reference： [1]Boettcher, Stephan; Thiem, Joachim [European Journal of Organic Chemistry, 2014, vol. 2014, # 3, p. 564 - 574]

15
[ 1607828-55-6 ]
[ 7240-90-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; morpholine / tetrahydrofuran / 20 °C 2: potassium carbonate; silver(I) acetate / 0.33 h / 90 - 100 °C 3: sodium methylate / methanol / 20 °C

Reference： [1]Boettcher, Stephan; Thiem, Joachim [European Journal of Organic Chemistry, 2014, vol. 2014, # 3, p. 564 - 574]

16
C₂₃H₂₃BrClNO₁₂ [ No CAS ]
[ 7240-90-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium carbonate; silver(I) acetate / 0.33 h / 90 - 100 °C 2: sodium methylate / methanol / 20 °C

Reference： [1]Boettcher, Stephan; Thiem, Joachim [European Journal of Organic Chemistry, 2014, vol. 2014, # 3, p. 564 - 574]

17
[ 125328-75-8 ]
[ 7240-90-6 ]

Yield	Reaction Conditions	Operation in experiment
87%	With sodium methylate In methanol at 20℃;
86%	With potassium hydroxide In methanol at 25 - 28℃; for 1h;
86%	With potassium hydroxide In methanol at 20℃; for 1h;	2.2 (2) Deprotection reaction To a solution of (1-acetyl-5-bromo-4-chloroindol-3-yl) 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside (300 mg, 0.485 mmol) in anhydrous methanol (9 mL) was added KOH methanol solution (1 mol / L, 72.7 μL, 0.15 eq) and the mixture was stirred at room temperature for 1 h. The precipitate was filtered with suction and the filtrate was concentrated. The combined filtrate was filtered, washed with an appropriate amount of dichloromethane to remove indigo, and dried in vacuo to give the title compound (171 mg, 86% yield) as a white powder. Its structure is shown in Formula 3b, 5-bromo-4-chloroindol-3-yl) β-D-galactopyranoside (X-Gal)

Reference： [1]Boettcher, Stephan; Thiem, Joachim [European Journal of Organic Chemistry, 2014, vol. 2014, # 3, p. 564 - 574]
[2]Wei, Xianhu; Wu, Qingping; Zhang, Jumei; Zhang, Youxiong; Guo, Weipeng; Chen, Moutong; Gu, Qihui; Cai, Zhihe; Lu, Mianfei [Chemical Communications, 2017, vol. 53, # 1, p. 103 - 106]
[3]Current Patent Assignee: GUANGDONG HUANKAI MICROBIAL SCI & TECHNOLOGY CO LTD; GUANGDONG ACADEMY OF SCIENCES - CN106432369, 2017, A Location in patent: Paragraph 0054; 0055; 0056; 0057

18
C₁₆H₁₇BrClNO₈ [ No CAS ]
[ 7240-90-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: sodium hydroxide / water / 40 - 45 °C 2: potassium carbonate; silver(I) acetate / 1 h / 110 °C 3: sodium methylate / methanol / 20 °C

Reference： [1]Boettcher, Stephan; Thiem, Joachim [European Journal of Organic Chemistry, 2014, vol. 2014, # 3, p. 564 - 574]

19
C₁₅H₁₅BrClNO₈ [ No CAS ]
[ 7240-90-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium carbonate; silver(I) acetate / 1 h / 110 °C 2: sodium methylate / methanol / 20 °C

Reference： [1]Boettcher, Stephan; Thiem, Joachim [European Journal of Organic Chemistry, 2014, vol. 2014, # 3, p. 564 - 574]

20
[ 627531-47-9 ]
[ 7240-90-6 ]

Reference： [1]European Journal of Organic Chemistry,2014,vol. 2014,p. 564 - 574

21
[ 125328-80-5 ]
[ 7240-90-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 10 steps 1.1: potassium permanganate; magnesium sulfate / water / 5.5 h / Reflux 2.1: sodium hydroxide; water / 4 h / Reflux 3.1: pyridine / dichloromethane; acetonitrile / 3.5 h / 45 °C / Inert atmosphere 4.1: sodium hydride / N,N-dimethyl-formamide / 0.75 h / Inert atmosphere; Cooling with ice 4.2: Inert atmosphere 5.1: sodium hydride / 6.5 h / 20 °C / Inert atmosphere 6.1: potassium <i>tert</i>-butylate / diethyl ether / 2 h / 40 - 45 °C / Inert atmosphere 7.1: tetra(n-butyl)ammonium hydrogensulfate; potassium carbonate / water; dichloromethane / 20 °C 8.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; morpholine / tetrahydrofuran / 20 °C 9.1: potassium carbonate; silver(I) acetate / 0.33 h / 90 - 100 °C 10.1: sodium methylate / methanol / 20 °C

Reference： [1]Boettcher, Stephan; Thiem, Joachim [European Journal of Organic Chemistry, 2014, vol. 2014, # 3, p. 564 - 574]

22
[ 7240-90-6 ]
[ 59-23-4 ]
[ 29245-44-1 ]

Yield	Reaction Conditions	Operation in experiment
	With TREHALOSE; β-galactosidase; agarose In water at 37℃; Enzymatic reaction;	6 Example 6 Injectable Needles Containing a Drug in Preformulated Solid Microparticles Dispersed in a Polymeric Matrix Water soluble microparticles with particle size between 1 and 10 μm and a final dry content of 98 wt. % trehalose, 2 wt. % of poly(N-vinylpyrrolidone), and 100 mU/g of β-galactosidase as a model drug, are pre-formulated by spray drying. A polymerizable paste is prepared from 200 mg microparticles and 1 mL of a mixture of diethyleneglycol diacrylate (70 wt. %), 2-hydroxyethyl methacrylate (29 wt. %), (2-N,N-dimethylamino)ethyl methacrylate (0.7 wt. %) and camphorquinone (0.2 wt. %). The polymerizable paste is extruded into a transparent silicone tube of 1 mm inner diameter and irradiated with blue-violet light for 10 minutes to promote photo-polymerization. The silicone tube containing the polymerized material is cut into 7 mm length sections. The injectable needles are removed from the tube and incubated at 4° C. and 45° C. for 4 weeks. (0189) To evaluate β-galactosidase activity needles were injected into a 2% agarose gel containing 100 μg/ml of X-Gal (5-bromo-4-chloro-3-indolyl-β-D-galactopyranoside) and maintained at 37° C. In a few minutes a blue colour is observed in the vicinity of the injectable needles due to the release of β-galactosidase and transformation of the X-Gal substrate by the β-galactosidase enzymatic action, as illustrated in FIG. 4. No significant difference in the ability to induce a colour change from needles incubated at 4° C. and 45° C. indicates effective stabilization of the model drug.

Reference： [1]Current Patent Assignee: SCIENCE TO BUSINESS FOUNDATION; HELICON MEDICAL SL - US9271927, 2016, B2 Location in patent: Page/Page column 22

23
[ 7240-90-6 ]
C₈H₄BrClNO^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With β-galactosidase In aq. phosphate buffer; dimethyl sulfoxide at 37℃; for 0.583333h; Enzymatic reaction;

Reference： [1]Gu, Kaizhi; Xu, Yisheng; Li, Hui; Guo, Zhiqian; Zhu, Shaojia; Zhu, Shiqin; Shi, Ping; James, Tony D.; Tian, He; Zhu, Wei-Hong [Journal of the American Chemical Society, 2016, vol. 138, # 16, p. 5334 - 5340]

24
[ 116270-39-4 ]
[ 3068-32-4 ]
[ 7240-90-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: potassium phosphate; tetrabutylammomium bromide / dichloromethane; water / 0.17 h / 25 - 28 °C / Inert atmosphere 1.2: 4 h / 25 - 28 °C / Inert atmosphere 2.1: potassium hydroxide / methanol / 1 h / 25 - 28 °C
	Multi-step reaction with 2 steps 1.1: potassium phosphate / dichloromethane; water / 0.17 h / 20 °C / Inert atmosphere 1.2: 4 h 2.1: potassium hydroxide / methanol / 1 h / 20 °C

Reference： [1]Wei, Xianhu; Wu, Qingping; Zhang, Jumei; Zhang, Youxiong; Guo, Weipeng; Chen, Moutong; Gu, Qihui; Cai, Zhihe; Lu, Mianfei [Chemical Communications, 2017, vol. 53, # 1, p. 103 - 106]
[2]Current Patent Assignee: GUANGDONG HUANKAI MICROBIAL SCI & TECHNOLOGY CO LTD; GUANGDONG ACADEMY OF SCIENCES - CN106432369, 2017, A

25
[ 7240-90-6 ]
[ 19342-33-7 ]
C₂₅H₃₁BrClN₂O₁₄^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With photobacterium species α2−6-sialyltransferase; magnesium chloride In N,N-dimethyl-formamide at 30℃; for 18h; Enzymatic reaction;

Reference： [1]McArthur, John B.; Yu, Hai; Tasnima, Nova; Lee, Christie M.; Fisher, Andrew J.; Chen, Xi [ACS Chemical Biology, 2018, vol. 13, # 5, p. 1228 - 1234]

26
[ 7240-90-6 ]
N-Acetyl-D-glucosamine [ No CAS ]
cytidine 5′-triphosphate disodium salt [ No CAS ]
[ 57-60-3 ]
C₂₅H₂₉⁽²⁾H₃BrClN₂O₁₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56 mg	With E_. coli sialic acid aldolase; Campylobacter jejuni Sialyltransferase; Neisseria meningitidis CMP-Sialic Acid Synthase; Pedobacter heparinus N-Acetyl-D-Glucosamine-2-Epimerase; water-d2; magnesium chloride In N,N-dimethyl-formamide at 37℃; Further stages;	4.3. One-Pot Four-Enzyme Synthesis of d3-Sialosides The synthesis of 9a was based on a procedure described previously [23,32], with slight modifications and performing the enzymatic reaction in D2O instead of H2O; in brief, the one-pot four-enzyme reaction was carried out using a lyophilized mixture of MES buffer (50 mM, pH 6.5) contained GlcNAc (10 mmol), CTP (0.15 mmol), pyruvate (0.25 mmol), MgCl2 (0.05 mmol), PhGn2E(5 mU), EcNeuAld (5 mU), NmCTT (5 mU) and CjSiaT3 (5 mU). The mixture was dissolved in D2O(50 mL), and then X-Gal (0.1 mmol, dissolved in 0.5 mL of DMF) was added. The reaction mixture was then incubated at 37 °C for 48-96 h until more than 80% product formation was observed (based on the amount of X-Gal; HPLC analysis was performed with 20 L sample aliquots). In cases were no complete conversion was observed, residual X-Gal was removed by adding E. coli-galactosidase(10 U). The supernatant was concentrated and purified using solid phase extraction (RP-C18, Supelco,Bellefonte, PA, USA, 500 mg resin fill, yielding 56 mg of sialoside). For the synthesis of 9b, GlcNGc(10 mmol) was used instead of GlcNAc and yielded 72 mg of sialoside. For the biosynthesis of the non-deuterated sialosides, D2O was replaced with H2O, yielding 59 mg for X-Gal-α-2,3-Neu5Ac and 69 mg for X-Gal-α-2,3-Neu5Gc.

Reference： [1]Cai, Zhi-P.; Conway, Louis P.; Huang, Ying Y.; Wang, Wen J.; Laborda, Pedro; Wang, Ting; Lu, Ai M.; Yao, Hong L.; Huang, Kun; Flitsch, Sabine L.; Liu, Li; Voglmeir, Josef [Molecules, 2019, vol. 24, # 7]

27
[ 7240-90-6 ]
N-Acetyl-D-glucosamine [ No CAS ]
cytidine 5′-triphosphate disodium salt [ No CAS ]
[ 57-60-3 ]
C₂₅H₃₂BrClN₂O₁₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59 mg	With E_. coli sialic acid aldolase; Campylobacter jejuni Sialyltransferase; Neisseria meningitidis CMP-Sialic Acid Synthase; Pedobacter heparinus N-Acetyl-D-Glucosamine-2-Epimerase; water; magnesium chloride In N,N-dimethyl-formamide at 37℃; Further stages;	4.3. One-Pot Four-Enzyme Synthesis of d3-Sialosides General procedure: The synthesis of 9a was based on a procedure described previously [23,32], with slight modifications and performing the enzymatic reaction in D2O instead of H2O; in brief, the one-pot four-enzyme reaction was carried out using a lyophilized mixture of MES buffer (50 mM, pH 6.5) contained GlcNAc (10 mmol), CTP (0.15 mmol), pyruvate (0.25 mmol), MgCl2 (0.05 mmol), PhGn2E(5 mU), EcNeuAld (5 mU), NmCTT (5 mU) and CjSiaT3 (5 mU). The mixture was dissolved in D2O(50 mL), and then X-Gal (0.1 mmol, dissolved in 0.5 mL of DMF) was added. The reaction mixture was then incubated at 37 °C for 48-96 h until more than 80% product formation was observed (based on the amount of X-Gal; HPLC analysis was performed with 20 L sample aliquots). In cases were no complete conversion was observed, residual X-Gal was removed by adding E. coli-galactosidase(10 U). The supernatant was concentrated and purified using solid phase extraction (RP-C18, Supelco,Bellefonte, PA, USA, 500 mg resin fill, yielding 56 mg of sialoside). For the synthesis of 9b, GlcNGc(10 mmol) was used instead of GlcNAc and yielded 72 mg of sialoside. For the biosynthesis of the non-deuterated sialosides, D2O was replaced with H2O, yielding 59 mg for X-Gal-α-2,3-Neu5Ac and 69 mg for X-Gal-α-2,3-Neu5Gc.

28
[ 7240-90-6 ]
cytidine 5′-triphosphate disodium salt [ No CAS ]
[ 31505-80-3 ]
[ 57-60-3 ]
C₂₅H₂₉⁽²⁾H₃BrClN₂O₁₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72 mg	With E_. coli sialic acid aldolase; Campylobacter jejuni Sialyltransferase; Neisseria meningitidis CMP-Sialic Acid Synthase; Pedobacter heparinus N-Acetyl-D-Glucosamine-2-Epimerase; water-d2; magnesium chloride In N,N-dimethyl-formamide at 37℃; Further stages;	4.3. One-Pot Four-Enzyme Synthesis of d3-Sialosides General procedure: The synthesis of 9a was based on a procedure described previously [23,32], with slight modifications and performing the enzymatic reaction in D2O instead of H2O; in brief, the one-pot four-enzyme reaction was carried out using a lyophilized mixture of MES buffer (50 mM, pH 6.5) contained GlcNAc (10 mmol), CTP (0.15 mmol), pyruvate (0.25 mmol), MgCl2 (0.05 mmol), PhGn2E(5 mU), EcNeuAld (5 mU), NmCTT (5 mU) and CjSiaT3 (5 mU). The mixture was dissolved in D2O(50 mL), and then X-Gal (0.1 mmol, dissolved in 0.5 mL of DMF) was added. The reaction mixture was then incubated at 37 °C for 48-96 h until more than 80% product formation was observed (based on the amount of X-Gal; HPLC analysis was performed with 20 L sample aliquots). In cases were no complete conversion was observed, residual X-Gal was removed by adding E. coli-galactosidase(10 U). The supernatant was concentrated and purified using solid phase extraction (RP-C18, Supelco,Bellefonte, PA, USA, 500 mg resin fill, yielding 56 mg of sialoside). For the synthesis of 9b, GlcNGc(10 mmol) was used instead of GlcNAc and yielded 72 mg of sialoside. For the biosynthesis of the non-deuterated sialosides, D2O was replaced with H2O, yielding 59 mg for X-Gal-α-2,3-Neu5Ac and 69 mg for X-Gal-α-2,3-Neu5Gc.

29
[ 7240-90-6 ]
cytidine 5′-triphosphate disodium salt [ No CAS ]
[ 31505-80-3 ]
[ 57-60-3 ]
C₂₅H₃₂BrClN₂O₁₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69 mg	With E_. coli sialic acid aldolase; Campylobacter jejuni Sialyltransferase; Neisseria meningitidis CMP-Sialic Acid Synthase; Pedobacter heparinus N-Acetyl-D-Glucosamine-2-Epimerase; water; magnesium chloride In N,N-dimethyl-formamide at 37℃; Further stages;	4.3. One-Pot Four-Enzyme Synthesis of d3-Sialosides General procedure: The synthesis of 9a was based on a procedure described previously [23,32], with slight modifications and performing the enzymatic reaction in D2O instead of H2O; in brief, the one-pot four-enzyme reaction was carried out using a lyophilized mixture of MES buffer (50 mM, pH 6.5) contained GlcNAc (10 mmol), CTP (0.15 mmol), pyruvate (0.25 mmol), MgCl2 (0.05 mmol), PhGn2E(5 mU), EcNeuAld (5 mU), NmCTT (5 mU) and CjSiaT3 (5 mU). The mixture was dissolved in D2O(50 mL), and then X-Gal (0.1 mmol, dissolved in 0.5 mL of DMF) was added. The reaction mixture was then incubated at 37 °C for 48-96 h until more than 80% product formation was observed (based on the amount of X-Gal; HPLC analysis was performed with 20 L sample aliquots). In cases were no complete conversion was observed, residual X-Gal was removed by adding E. coli-galactosidase(10 U). The supernatant was concentrated and purified using solid phase extraction (RP-C18, Supelco,Bellefonte, PA, USA, 500 mg resin fill, yielding 56 mg of sialoside). For the synthesis of 9b, GlcNGc(10 mmol) was used instead of GlcNAc and yielded 72 mg of sialoside. For the biosynthesis of the non-deuterated sialosides, D2O was replaced with H2O, yielding 59 mg for X-Gal-α-2,3-Neu5Ac and 69 mg for X-Gal-α-2,3-Neu5Gc.

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[ CAS No. 7240-90-6 ] {[proInfo.proName]}

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[ 7240-90-6 ] Synthesis Path-Downstream 1~29

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