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13929-35-6

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13929-35-6 Usage

Uses

Different sources of media describe the Uses of 13929-35-6 differently. You can refer to the following data:
1. A Rifamycin (R508200) derivative as antibacterial agent.
2. Rifamycin B (Rifaximin EP Impurity B) is a Rifamycin (R508200) derivative as antibacterial agent.

Purification Methods

Rifamycin B forms yellow needles from *C6H6. Its solubilities are: H2O (0,027%), MeOH (2.62%) and EtOH (0.44%). It has UV max at 223, 304 and 245nm (A 1cm 555, 275 and 220). [Oppolzer & Prelog Helv Chim Acta 56 2287 1973, Oppolzer et al. Experientia 20 336 1964, X-ray: Brufani et al. Experientia 20 339 1964.]

Check Digit Verification of cas no

The CAS Registry Mumber 13929-35-6 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,3,9,2 and 9 respectively; the second part has 2 digits, 3 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 13929-35:
(7*1)+(6*3)+(5*9)+(4*2)+(3*9)+(2*3)+(1*5)=116
116 % 10 = 6
So 13929-35-6 is a valid CAS Registry Number.
InChI:InChI=1/C39H49NO14/c1-17-11-10-12-18(2)38(49)40-24-15-26(51-16-27(42)43)28-29(34(24)47)33(46)22(6)36-30(28)37(48)39(8,54-36)52-14-13-25(50-9)19(3)35(53-23(7)41)21(5)32(45)20(4)31(17)44/h10-15,17,19-21,25,31-32,35,44-47H,16H2,1-9H3,(H,40,49)(H,42,43)/b11-10+,14-13+,18-12+/t17-,19-,20+,21-,25-,31-,32+,35+,39-/m0/s1

13929-35-6 Well-known Company Product Price

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  • Sigma-Aldrich

  • (R0900000)  Rifamycin B  European Pharmacopoeia (EP) Reference Standard

  • 13929-35-6

  • R0900000

  • 1,880.19CNY

  • Detail

13929-35-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name rifamycin B

1.2 Other means of identification

Product number -
Other names Rifamycin, 4-O-(carboxymethyl)-

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:13929-35-6 SDS

13929-35-6Synthetic route

D-Glucose
2280-44-6

D-Glucose

Amycolatopsis mediterranei ATCC 21789/pJG8.219A

Amycolatopsis mediterranei ATCC 21789/pJG8.219A

A

5-deoxy-5-amino-shikimic acid
178948-66-8

5-deoxy-5-amino-shikimic acid

B

Rifamycin B
13929-35-6

Rifamycin B

Conditions
ConditionsYield
With oxygen In various solvent(s) at 28℃; for 288h; Microbiological reaction;A 0.4%
B n/a
Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: transketolase Rif15; cytochrome P450 enzyme Rif16; thiamine pyrophosphate; magnesium chloride / aq. buffer / 4 h / 28 °C / pH 7.4 / Enzymatic reaction
2: ferredoxin seFdx; ferredoxin reductasese FdR; NADPH; cytochrome P450 enzyme Rif16 / aq. buffer / 4 h / 28 °C / Enzymatic reaction
View Scheme
rifamycin L

rifamycin L

Rifamycin B
13929-35-6

Rifamycin B

Conditions
ConditionsYield
With cytochrome P450 enzyme Rif16; ferredoxin reductasese FdR; ferredoxin seFdx; NADPH In aq. buffer at 28℃; for 4h; Reagent/catalyst; Enzymatic reaction;3 mg
rifamycin SV
6998-60-3

rifamycin SV

Rifamycin B
13929-35-6

Rifamycin B

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: magnesium chloride; oxygen / water
2: transketolase Rif15; cytochrome P450 enzyme Rif16; thiamine pyrophosphate; magnesium chloride / aq. buffer / 4 h / 28 °C / pH 7.4 / Enzymatic reaction
3: ferredoxin seFdx; ferredoxin reductasese FdR; NADPH; cytochrome P450 enzyme Rif16 / aq. buffer / 4 h / 28 °C / Enzymatic reaction
View Scheme
Rifamycin B
13929-35-6

Rifamycin B

rifamycin O
14487-05-9

rifamycin O

Conditions
ConditionsYield
With air Ambient temperature;80%
(R)-2-fluoro-N-(1-((5-fluoro-2-(piperazin-1-yl)phenyl)amino)-1-oxo-3-phenylpropan-2-yl-3,3-d2)benzamide

(R)-2-fluoro-N-(1-((5-fluoro-2-(piperazin-1-yl)phenyl)amino)-1-oxo-3-phenylpropan-2-yl-3,3-d2)benzamide

Rifamycin B
13929-35-6

Rifamycin B

C65H71(2)H2F2N5O15

C65H71(2)H2F2N5O15

Conditions
ConditionsYield
Stage #1: Rifamycin B With dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; for 1.5h; Inert atmosphere;
Stage #2: (R)-2-fluoro-N-(1-((5-fluoro-2-(piperazin-1-yl)phenyl)amino)-1-oxo-3-phenylpropan-2-yl-3,3-d2)benzamide With dmap; triethylamine In N,N-dimethyl-formamide at 80℃; for 6h; Inert atmosphere;
40%
C31H53N9O14

C31H53N9O14

Rifamycin B
13929-35-6

Rifamycin B

C70H100N10O27

C70H100N10O27

Conditions
ConditionsYield
Stage #1: Rifamycin B With dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 25℃; for 1h;
Stage #2: C31H53N9O14 With dmap In N,N-dimethyl-formamide at 25℃; for 1h;
3.3%
pyrrolidine
123-75-1

pyrrolidine

Rifamycin B
13929-35-6

Rifamycin B

O4-(2-oxo-2-pyrrolidin-1-yl-ethyl)-rifamycin
13929-40-3

O4-(2-oxo-2-pyrrolidin-1-yl-ethyl)-rifamycin

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In tetrahydrofuran
piperidine
110-89-4

piperidine

Rifamycin B
13929-35-6

Rifamycin B

O4-(2-oxo-2-piperidin-1-yl-ethyl)-rifamycin
14487-04-8

O4-(2-oxo-2-piperidin-1-yl-ethyl)-rifamycin

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In tetrahydrofuran
morpholine
110-91-8

morpholine

Rifamycin B
13929-35-6

Rifamycin B

O4-(2-morpholin-4-yl-2-oxo-ethyl)-rifamycin
14150-54-0

O4-(2-morpholin-4-yl-2-oxo-ethyl)-rifamycin

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In tetrahydrofuran
2,5-dimethylpyrrolide
3378-71-0

2,5-dimethylpyrrolide

Rifamycin B
13929-35-6

Rifamycin B

O4-[2-((2Ξ)-2r,5ξ-dimethyl-pyrrolidin-1-yl)-2-oxo-ethyl]-rifamycin
38123-17-0

O4-[2-((2Ξ)-2r,5ξ-dimethyl-pyrrolidin-1-yl)-2-oxo-ethyl]-rifamycin

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In tetrahydrofuran
3-methylmorpholine
42185-06-8

3-methylmorpholine

Rifamycin B
13929-35-6

Rifamycin B

O4-[2-((Ξ)-3-methyl-morpholin-4-yl)-2-oxo-ethyl]-rifamycin
38123-18-1

O4-[2-((Ξ)-3-methyl-morpholin-4-yl)-2-oxo-ethyl]-rifamycin

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In tetrahydrofuran
2,6-dimethylmorpholine
123-57-9

2,6-dimethylmorpholine

Rifamycin B
13929-35-6

Rifamycin B

O4-[2-((3Ξ)-3r,5ξ-dimethyl-morpholin-4-yl)-2-oxo-ethyl]-rifamycin
55372-15-1

O4-[2-((3Ξ)-3r,5ξ-dimethyl-morpholin-4-yl)-2-oxo-ethyl]-rifamycin

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In tetrahydrofuran
(2-hydroxyethyl)(methyl)amine
109-83-1

(2-hydroxyethyl)(methyl)amine

Rifamycin B
13929-35-6

Rifamycin B

O4-{[(2-hydroxy-ethyl)-methyl-carbamoyl]-methyl}-rifamycin
55447-17-1

O4-{[(2-hydroxy-ethyl)-methyl-carbamoyl]-methyl}-rifamycin

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In tetrahydrofuran
methyl-morpholin-4-yl-amine
5824-80-6

methyl-morpholin-4-yl-amine

Rifamycin B
13929-35-6

Rifamycin B

O4-[(methyl-morpholin-4-yl-carbamoyl)-methyl]-rifamycin
17863-72-8

O4-[(methyl-morpholin-4-yl-carbamoyl)-methyl]-rifamycin

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In tetrahydrofuran
4-methylpiperidin
626-58-4

4-methylpiperidin

Rifamycin B
13929-35-6

Rifamycin B

O4-[2-(4-methyl-piperidin-1-yl)-2-oxo-ethyl]-rifamycin
26242-20-6

O4-[2-(4-methyl-piperidin-1-yl)-2-oxo-ethyl]-rifamycin

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In tetrahydrofuran
hexamethylene imine
111-49-9

hexamethylene imine

Rifamycin B
13929-35-6

Rifamycin B

O4-(2-azepan-1-yl-2-oxo-ethyl)-rifamycin
13929-37-8

O4-(2-azepan-1-yl-2-oxo-ethyl)-rifamycin

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In tetrahydrofuran
propylamine
107-10-8

propylamine

Rifamycin B
13929-35-6

Rifamycin B

O4-(propylcarbamoyl-methyl)-rifamycin
55372-05-9

O4-(propylcarbamoyl-methyl)-rifamycin

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In tetrahydrofuran
N-(1-Propyl)propargylamine
42268-62-2

N-(1-Propyl)propargylamine

Rifamycin B
13929-35-6

Rifamycin B

O4-[(propyl-prop-2-ynyl-carbamoyl)-methyl]-rifamycin
38128-71-1

O4-[(propyl-prop-2-ynyl-carbamoyl)-methyl]-rifamycin

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In tetrahydrofuran
N-n-butyl-N-methylamine
110-68-9

N-n-butyl-N-methylamine

Rifamycin B
13929-35-6

Rifamycin B

O4-[(butyl-methyl-carbamoyl)-methyl]-rifamycin
16784-08-0

O4-[(butyl-methyl-carbamoyl)-methyl]-rifamycin

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In tetrahydrofuran
diisobutylamine
110-96-3

diisobutylamine

Rifamycin B
13929-35-6

Rifamycin B

O4-(diisobutylcarbamoyl-methyl)-rifamycin
16784-05-7

O4-(diisobutylcarbamoyl-methyl)-rifamycin

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In tetrahydrofuran
N-methyl-N-(piperidin-1-yl)amine
5824-74-8

N-methyl-N-(piperidin-1-yl)amine

Rifamycin B
13929-35-6

Rifamycin B

O4-[(methyl-piperidin-1-yl-carbamoyl)-methyl]-rifamycin
55372-20-8

O4-[(methyl-piperidin-1-yl-carbamoyl)-methyl]-rifamycin

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In tetrahydrofuran
N-methylcyclopentylamine
2439-56-7

N-methylcyclopentylamine

Rifamycin B
13929-35-6

Rifamycin B

O4-[(cyclopentyl-methyl-carbamoyl)-methyl]-rifamycin
17607-41-9

O4-[(cyclopentyl-methyl-carbamoyl)-methyl]-rifamycin

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In tetrahydrofuran
N-methylcyclohexylamine
100-60-7

N-methylcyclohexylamine

Rifamycin B
13929-35-6

Rifamycin B

O4-[(cyclohexyl-methyl-carbamoyl)-methyl]-rifamycin
17863-71-7

O4-[(cyclohexyl-methyl-carbamoyl)-methyl]-rifamycin

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In tetrahydrofuran
N-(2-ethylamino)piperidine
216080-58-9

N-(2-ethylamino)piperidine

Rifamycin B
13929-35-6

Rifamycin B

O4-[(ethyl-piperidin-1-yl-carbamoyl)-methyl]-rifamycin
55372-21-9

O4-[(ethyl-piperidin-1-yl-carbamoyl)-methyl]-rifamycin

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In tetrahydrofuran
N-(2-cyanoethyl)-N-methylamine
693-05-0

N-(2-cyanoethyl)-N-methylamine

Rifamycin B
13929-35-6

Rifamycin B

O4-{[(2-cyano-ethyl)-methyl-carbamoyl]-methyl}-rifamycin
55447-18-2

O4-{[(2-cyano-ethyl)-methyl-carbamoyl]-methyl}-rifamycin

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In tetrahydrofuran
ethylpropylamine
20193-20-8

ethylpropylamine

Rifamycin B
13929-35-6

Rifamycin B

O4-[(ethyl-propyl-carbamoyl)-methyl]-rifamycin
16784-02-4

O4-[(ethyl-propyl-carbamoyl)-methyl]-rifamycin

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In tetrahydrofuran
N-Ethylmethylamine
624-78-2

N-Ethylmethylamine

Rifamycin B
13929-35-6

Rifamycin B

O4-[(ethyl-methyl-carbamoyl)-methyl]-rifamycin
17607-34-0

O4-[(ethyl-methyl-carbamoyl)-methyl]-rifamycin

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In tetrahydrofuran
N-methylpropan-2-amine
4747-21-1

N-methylpropan-2-amine

Rifamycin B
13929-35-6

Rifamycin B

O4-[(isopropyl-methyl-carbamoyl)-methyl]-rifamycin
38128-77-7

O4-[(isopropyl-methyl-carbamoyl)-methyl]-rifamycin

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In tetrahydrofuran
N-methyl-tert-butylamine
14610-37-8

N-methyl-tert-butylamine

Rifamycin B
13929-35-6

Rifamycin B

O4-[(tert-butyl-methyl-carbamoyl)-methyl]-rifamycin
55372-11-7

O4-[(tert-butyl-methyl-carbamoyl)-methyl]-rifamycin

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In tetrahydrofuran
N-ethylbutylamine
13360-63-9

N-ethylbutylamine

Rifamycin B
13929-35-6

Rifamycin B

O4-[(butyl-ethyl-carbamoyl)-methyl]-rifamycin
38128-76-6

O4-[(butyl-ethyl-carbamoyl)-methyl]-rifamycin

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In tetrahydrofuran
N'-ethyl-N,N-dimethyl-hydrazine
29559-82-8

N'-ethyl-N,N-dimethyl-hydrazine

Rifamycin B
13929-35-6

Rifamycin B

O4-(N-ethyl-N',N'-dimethyl-hydrazinocarbonylmethyl)-rifamycin
17607-48-6

O4-(N-ethyl-N',N'-dimethyl-hydrazinocarbonylmethyl)-rifamycin

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In tetrahydrofuran
1,1-dimethyl-2-n-propylhydrazine
52728-54-8

1,1-dimethyl-2-n-propylhydrazine

Rifamycin B
13929-35-6

Rifamycin B

O4-(N',N'-dimethyl-N-propyl-hydrazinocarbonylmethyl)-rifamycin
17607-49-7

O4-(N',N'-dimethyl-N-propyl-hydrazinocarbonylmethyl)-rifamycin

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In tetrahydrofuran

13929-35-6Relevant articles and documents

Deciphering the late steps of rifamycin biosynthesis

Qi, Feifei,Lei, Chao,Li, Fengwei,Zhang, Xingwang,Wang, Jin,Zhang, Wei,Fan, Zhen,Li, Weichao,Tang, Gong-Li,Xiao, Youli,Zhao, Guoping,Li, Shengying

, (2018/06/26)

Rifamycin-derived drugs, including rifampin, rifabutin, rifapentine, and rifaximin, have long been used as first-line therapies for the treatment of tuberculosis and other deadly infections. However, the late steps leading to the biosynthesis of the industrially important rifamycin SV and B remain largely unknown. Here, we characterize a network of reactions underlying the biosynthesis of rifamycin SV, S, L, O, and B. The two-subunit transketolase Rif15 and the cytochrome P450 enzyme Rif16 are found to mediate, respectively, a unique C-O bond formation in rifamycin L and an atypical P450 ester-to-ether transformation from rifamycin L to B. Both reactions showcase interesting chemistries for these two widespread and well-studied enzyme families.

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