CAS: 26395-99-3; 7-Amino-3-Methyl-8-Oxo-5-Thia-1-Azabicyclo[4.2.0]Oct-2-Ene-2-Carboxylic Acid

该化合物是一种双环β-光化化合物,作为甲状腺素抗生素合成的关键中间体,其结构具有一个对抗微生物活动至关重要的引信β-光化和二氢硫氨环系系统.该化合物的稳定性和再活性使其对衍生具有价值,能够生产对β-光化素具有更大抗药性的广谱抗生素.其精确的立体化学和功能组允许有针对性地修改,改善药用植物特性.由于其在开发高效和结构多样的甲状腺素衍生物方面的作用,该替代品在制药研究和工业应用中广泛使用.

结构式图片

相似化合物

79349-82-9 120709-09-3 22252-43-3

上下游产品

CAS号50370-12-2 头孢羟氨苄

合成工艺路线路线简述

  • 合成目标产物 7-Amino-3-Methyl-8-Oxo-5-Thia-1-Azabicyclo[4.2.0]Oct-2-Ene-2-Carboxylic Acid 主要起始原料 Cefathiamidine Impurity 5
  • (文献来源)合成步骤主要原料 Cefathiamidine Impurity 5
(6R)-7T-(2-Chloro-Acetylamino)-3-Methyl-8-Oxo-(6Rh)-5-Thia-1-Aza-Bicyclo[4.2.0]oct-2-Ene-2-Carboxylic Acid置于sodium Hydroxide,硫脲体系中,用 水 用作溶剂,化学反应生成7-氨基去乙酰氧基头孢烷酸
参考文献:7-Trichloroacetamido-3-Desacetoxy-Cephalosporanic Acid Esters
标题:7-Trichloroacetamido-3-Desacetoxy-Cephalosporanic Acid Esters
摘要:该发明提供了式为:##spc1## 其中r是保护羧基的基团,可以通过将r-和cl3C-Co-基团替换为氢原子来转化为7-氨基-3-去乙酰基头孢菌素酸的7-三氯乙酰胺基-3-去乙酰基头孢菌素酸衍生物.

海关参考信息

专利信息


专利号:EP-2173892-B8
优先权日:2007-07-27
标题:Process for the preparation of immobilised recombinant Penicillin Acylase biocatalyst from Achromobacter sp CCM 4824 expressed in E. coli BL21 CCM 7394 and its use for the synthesis of beta-lactam antiobiotics
发明人:DATLA ANUPAMA; RAJASEKAR VYASARAYANI WILLIAMS; KYSLIK PAVEL; BECKA STANISLAV; KRISHNAKANT ASHAR TRUPTI; YOGESH ZAMBRE SUJATA; NIKUNJ KUMAR
权利人:FERMENTA BIOTECH LTD
摘要:The present invention discloses isolation of Penicillin Acylase (PA) from Achromobacter sp CCM 4824 expressed in recombinant strain E. coli BL21 CCM 7394 bearing the recombinant plasmid pKXIP1 and processing of PA into biocatalyst useful for the industrial synthesis of antibiotics. More particularly the invention discloses a synthesis of semi-synthetic β-lactam antibiotics in the reaction mixture consisting of activated acyl-donor (D-p-hydroxyphenylglycine methyl ester or amide for Amoxicillin and Cefadroxil; D-phenylglycine methyl ester or amide for Ampicillin and Cephalexin) and nucleophile (6-APA or 7-ADCA) catalyzed by PA obtained from recombinant E. coli BL21 CCM 7394 as the biocatalyst.

专利号:US-2003044884-A1
优先权日:2000-10-11
标题:Synthesis of beta-lactam antibacterials using soluble side chain esters and enzyme acylase
发明人:USHER JOHN J; ROMANCIK GUNA
摘要:Disclosed is a process for the synthesis of β-lactam antibacterials using soluble side chain esters in the presence of enzyme acylase. Also disclosed are novel esters useful as reactants in said process.

专利号:US-5268271-A
优先权日:1989-12-12
标题 :Method for the synthesis of semi-synthetic antibiotics in thermodynamically controlled water-cosolvent organic miscible apolar systems by using penicillin G acylase
发明人:GUISAN SEIJAS JOSE M; FERNANDEZ LAFUENTE ROBERTO; ALVARO CAMPOS GREGORIO; BLANCO MARTIN ROSA M; MOLINA ROSELL CRISTINA
权利人:CONSEJO SUPERIOR INVESTIGACION
摘要:Synthesis of semi-synthetic monobactamic or β-Lactamic antibiotics by using derivatives stabilized by various methods of penicillin G acylase from various microbial sources according to a thermodynamically controlled strategy in monophase water/cosolvent organic apolar systems, wherein the concentration of the cosolvent varies between 30% and 90%, the temperature between -10° C. and 50° C., the pH between 4.5 and 8.5, with concentrations of the antibiotic nucleus between 0.5 an 875 mM and acyl donor between 0.2 mM and 1M, with a relationship antibiotic ring/activated or free acyl donor, using a buffer between 0 and 1M. Application to the pharmaceutical industry.

专利号:US-3758488-A
优先权日:1969-05-16
标题:Process for preparing thiazole derivatives
发明人:KUKOLJA S; MORIN R
权利人:LILLY CO ELI
摘要:PROCESS FOR PREPARING THIAZOLECARBONYLAMINO-SUBSTITUTED BUTENOIC ACIDS AND NEW THIAZOLECARBONYLAMINO-SUBSTITUTED OXAZOLONE COMPOUNDS, E.G., 2 - (N-(2-PHENOXYMETHYL-4THIAZOLYL)CARBONYL)AMINO-3-METHYL-BUTENOIC ACID, AND 2(2'' - PHENOXYMETHYL-4''-THIAZOLYL)-4-ISOPROPYLIDENE-5-OXAZOLONE BY TREATING A 2-(2-SUBSTITUTED-AMIDO-1-THIOACETYL-2ETHENYL)-4-ISOPROPYLIDENE-5-OXAZOLONE WITH ACID OR BASE, IN AN INERT ORGANIC SOLVENT, OR IN ADMIXTURE WITH THE ALCOHOL OF THE DESIRED ESTER, WHICH PRODUCTS OF THE PROCESS CAN BE USED AS ANTIBIOTICS AND ANTI-FUNGAL AGENTS, AS INTERMEDIATES IN THE SYNTHESIS OF PENICILLIN AND CEPHALOSPORIN COMPOUNDS AND AS ANTIRADIATION CHEMICALS.

专利号:EP-0458932-B1
优先权日:1989-12-12
标 题:Method for the synthesis of semi-synthetic antibiotics in thermodynamically controlled water-cosolvent organic miscible apolar systems by using penicillin g acylase

专利号:WO-2009016642-A1
优先权日:2007-07-27
标题 :Process for the preparation of immobilized recombinant penicillin acylase catalyst from achromobacter sp. ccm 4824 expressed in e. coli bl 21 ccm 7394 and its use for the synthesis of beta-lactam antibiotics
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合成参考文献


参考文献:10.1186/1472-6750-10-7
摘要:Maresová H, Marková Z, Valesová R, Sklenár J, Kyslík P. Heterologous expression of leader-less pga gene in Pichia pastoris: intracellular production of prokaryotic enzyme. BMC Biotechnol. 2010 Feb 03;10():7.
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