CAS: 37321-09-8; Apramycin

📜Benzyl N-[(2R,3S,4R,4Ar,6S,7R,8As)-2-[(2R,3R,4S,5R,6S)-5-Azido-3,4-Bis(Phenylmethoxy)-6-(Phenylmethoxymethyl)Oxan-2-Yl]Oxy-6-[(1R,2R,3S,4R,6S)-2,3-Dihydroxy-4,6-Bis(Phenylmethoxycarbonylamino)Cyclohexyl]Oxy-4-Hydroxy-7-(Phenylmethoxycarbonylamino)-2,3,4,4A,6,7,8,8A-octahydropyrano[3,2-B]Pyran-3-Yl]-N-Methylcarbamate置于钯 氢气体系中,用 1,4-二氧六环,水,溶剂黄146 用作溶剂,化学反应 2.0H,以74%的收率获得安普霉素
参考文献:Total Synthesis Of Aminoglycoside Antibiotics,Apramycin And Saccharocin (Ka-5685)
标题:Total Synthesis Of Aminoglycoside Antibiotics,Apramycin And Saccharocin (Ka-5685)
摘要:阿普拉霉素和蔗糖霉素(ka-5685)已从先前合成的尼阿霉素(3)合成.将烯丙基氯化镁添加到4-O-[3',4'-O-环己叉-2'-脱氧-2'-(对甲苯磺酰氨基)-α-D-葡六双醛-1',5'-吡喃糖基]-5,6-O-环己叉-1,3-二-N-对甲苯磺酰-2-脱氧链霉胺(由3通过6'-N-氧化物衍生得到),得到4-O-[3',4'-O-环己叉-2',7',8',9'-四脱氧-2'-(对甲苯磺酰氨基)-L-甘油和d-甘油-α-D-葡-8'-烯吡喃糖基]-5,6-O-环己叉-1,3-二-N-对甲苯磺酰-2-脱氧链霉胺,后者又转化为4-O-[(8's)-7'-N,6'-O-羰基-2',3',7'-三脱氧-8'-O-甲基-7'-(甲氨基)-2'-(对甲苯磺酰氨基)-D-甘油-α-D-别辛双醛-1',5':8',4'-双吡喃糖基]-5,6-O-环己叉-1,3-二-N-对甲苯磺酰-2-脱氧链霉胺(25),通过1-N-乙酰基-4-O-[3',6'-二-O-乙酰基-4',8'-无水-2',7'-二脱氧-2'-(对甲苯磺酰氨基)-L-甘油-α-D-葡-7'-烯吡喃糖基]-5,6-O-环己叉-1,3-二-N-对甲苯磺酰-2-脱氧链霉胺的叠氮化硝化和6'-羟基的差向异构化.25的连续脱保护得到阿普拉霉素,从中制备了1,2',3,7'-四(n-苄氧羰基)阿普拉霉素(28),以及28与4-叠氮-2,3,6-三-O-苄基-4-脱氧-β-D-吡喃葡糖基氟或2,3,4,6-四-O-苄基-β-D-吡喃葡糖基氟的糖基化,随后进行氢解,完成了全合成.
Doi:10.1246/bcsj.57.529

专利信息

专利号:US-10920229-B2
优先权日:2014-07-16
标 题:Method for improving heterologous synthesis of Escherichia coli into polyketides and use of same
发明人：WANG YONG; XIONG ZHIQIANG; SONG SHUJIE; LIU QIAOXIA; WANG JIANFENG
权利人:SHANGHAI INST BIOLOGICAL SCIENCES CAS; CAS CENTER FOR EXCELLENCE IN MOLECULAR PLANT SCIENCES
摘要:The present invention relates to a method for improving the heterologous synthesis of a polyketide by E. coli and use thereof. The yield of the polyketide heterologously synthesized by E. coli is significantly increased by attenuating the expression of seventy-two genes, such as sucC and talB, in a host strain, wherein the highest yield increase rate can reach 60% or more. Currently, erythromycin is the most clear model compound in the study on the biosynthesis of polyketids. The production strain of the present invention enables massive accumulation of 6-deoxyerythronolide (6-dEB), an erythromycin precursor, in the fermentation process, laying the foundation for the industrial production of the heterologous synthesis of erythromycin by E. coli.

专利号:US-9873905-B2
优先权日:2014-03-07
标题:Chemoenzymatic synthesis of trehalose analogs
发明人：SWARTS BENJAMIN M; WOODRUFF PETER
权利人:CENTRAL MICHIGAN UNIV; UNIV OF MAINE SYSTEM
摘要:The present invention provides methods of synthesizing trehalose analogs; methods of detecting mycobacteria, and trehalose analogs.

专利号:US-2008044860-A1
优先权日:2003-11-28
标题 :Polyketides and Their Synthesis
发明人：GAISSER SABINE; HAYDOCK STEPHEN FREDERICK; LEADLAY PETER FRANCIS; MCARTHUR HAMISH ALASTAIR IRVIN
权利人:GAISSER SABINE; HAYDOCK STEPHEN FREDERICK; LEADLAY PETER FRANCIS; MCARTHUR HAMISH ALASTAIR IRVIN
摘要:Macrolides particularly erythromycins and azithromycins, having O-mycaminosyl or O-angolosaminyl groups, particularly at the 5 -position, are produced using a gene cassette comprising a combination of genes which, in an appropriate strain background, are able to direct the synthesis of mycaminose or angolosamine and to direct its subsequent transfer to an aglycone or pseudoaglycone. Synthetic genes may comprise one or more of angMIII, angMI, angB, angAI, angAII, angorf14, angorf4, tylMIII, tylMI, tylB, tylAI, tylAII, eryCVI, spnO, eryBVI, eryK, tyl Ia and ery G. Glycosyltransfer genes may comprise one or more of eryCIII, tylMII, angMII, desVII, eryBV, spnP and midI.

专利号:US-11981938-B2
优先权日:2017-10-05
标 题 :Microorganisms and methods for the fermentation of cannabinoids
发明人：SZAMECZ BELA KRISZTIAN; VARSZEGI SZILVIA; NEMETH ATTILA; SZABO LORAND; KUMAR ABHINAV
权利人:ELESZTO GENETIKA INC
摘要:Disclosed herein are microorganism and methods that can be used for the synthesis of cannabigerolic acid (CBGA) and cannabinoids. The methods disclosed can be used to produce CBGA, Δ9-tetrahydrocannabinolic acid (THCA), cannabidiolic acid (CBDA), cannabichromenic acid (CBCA), Δ9-tetrahydrocannabinol (THC), cannabidiol (CBD), cannabichromene (CBC). Enzymes useful for the synthesis of CBGA and cannabinoids, include but are not limited to acyl activating enzyme (AAE1), polyketide synthase (PKS), olivetolic acid cyclase (OAC), prenyltransferase (PT), THCA synthase (THCAS), CBDA synthase (CBDAS), CBCA synthase (CBCAS), HMG-Co reductase (HMG1), and/or farnesyl pyrophosphate synthetase (ERG20). The microorganisms can also have one or more genes disrupted, such as gene that that controls beta oxidation of long chain fatty acids.

专利号:US-2022170057-A1
优先权日:2019-04-11
标题:Microorganisms and methods for the fermentation of cannabinoids
发明人：SZAMECZ BELA KRISZTIAN; VARSZEGI SZILVIA; NEMETH ATTILA; SZABO LORAND
权利人:ELESZTO GENETIKA INC
摘要:Disclosed herein are microorganism and methods that can be used for the synthesis of cannabigerolic acid (CBGA) and cannabinoids. The methods disclosed can be used to produce CBGA, Δ 9 -tetrahydrocannabinolic acid (THCA), cannabidiolic acid (CBDA), cannabichromenic acid (CBGA), Δ 9 -tetrahydrocannabivarinic acid (THCVA), cannabidivarinic acid (CBDVA), cannabichromevarinic acid (CBCVA), Δ 9 -tetrahydrocannabinol (THC), cannabidiol (CBD), cannabichromene (CBC). Enzymes useful for the synthesis of CBGA and cannabinoids, include but are not limited to acyl activating enzyme (AAE1), polyketide synthase (PKS), olivetolic acid cyclase (OAC), prenyltransferase (PT), THCA synthase (THCAS), CBDA synthase (CBDAS), CBC A synthase (CBCAS), HMG-Co reductase (HMG1), and/or famesyl pyrophosphate synthetase (ERG20). The microorganisms can also have one or more genes disrupted, such as gene that that controls beta oxidation of long chain fatty acids.

专利号:US-7595156-B2
优先权日:2003-10-23
标 题:Genes for synthesis of FR-008 polyketides
发明人：LEE SANG YUP; DENG ZIXIN; CHEN SHI; JEONG KI JUN; ZHOU XIUFEN
权利人:KOREA ADVANCED INST SCI & TECH
摘要:The present invention relates to the base sequence of whole genes involved in the biosynthesis of FR-008 polyketides derived from Streptomyces sp. FR-008. This base sequence comprises genes coding for ketosynthase (KS), acyl transferase (AT), acyl carrier protein (ACP), ketoreductase (KR), dehydratase (DH) and enoyl reductase (ER) domains, and genes coding for modifier enzymes, such as ABC transporter, cytochrome P450 monooxygenase, ferredoxin, thioesterase, sugar synthetic protein, FAD-dependent monooxygenase, 4-amino-4-deoxychorismate (ADC) synthase and ADC lyase. The gene base sequence according to the present invention can be used to increase the productivity of the existing FR-008 polyketides or produce new FR-008 polyketides, through modification of its parts.