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TheprofessionalEnglishofpharmaceuticalengineeringWangXinliangEastChinauniversityofscienceandtechnology13.02.2012第一頁,共81頁。FinalexaminationTwoparts:gradeofdailystudy(30%)attendanceratehomeworkothers(exercise,middleexamination)gradeoffinalexamination(70%)Thecontentofexamination第二頁,共81頁。ThecontentofexaminationDegreetest

50%basicEnglish

50%professionalEnglish

word:translationfromEnglishtoChinese(5points)translationfromChinesetoEnglish(5points)Translation:(40points)4paragraphswhichincludeabout250wordsineachofthem.payattentiontoonly125to150wordsineachparagraphneedtobetranslated.These4paragraphsarenotsimplesentence.第三頁,共81頁。HowtolearntheprofessionalEnglishMastersomeskillsMasterthenecessaryknowledgeWhatisthemostimportantthingmorereading,morespeaking,morewriting第四頁,共81頁。Whatistheimportantthinginthiscourseremembertheword?translatesentencebysentence?learnmoreprofessionalknowledge?YoudaoDict有道(yǒudào)詞典HowtoteachtheprofessionalEnglish第五頁,共81頁。Crocinyellow(藏花素),whichisextractedfromGardeniajasminoidesEllis(梔子(zhīzǐ)),iswidelyusedasanaturalfoodcolorantinAsiancountries,whileGardeniaextracthasbeenusedinChinesetraditionalmedicine(CTM)forcuringanumberofailments[3].Thesecrocetin(藏紅花酸)derivatives,whicharedifferentfrommostfamiliesofcarotenoids(類胡蘿卜素),areknownfortheircoloringpropertiesowingtotheirpeculiarwater-solublebehavior[4].Numerousstudieshavedealtwiththecomponentstructuresofyellowpigmentextractsisolatedfromgardeniafruits[4–8],theirspectroscopiccharacterizationandradical-scavengingactivity[4,9],dataconcerningtheconcentrationofmajorcomponentsforthedeterminationofoptimaltimeofharvestandextractionprocess[10,11].第六頁,共81頁。ThecontentofthiscourseIntroducesomeskillsoftranslationanddosomeexerciseintheclassroom.SummarizesomeregulationsintheprofessionalEnglish.Learnthetext.Discusssometopics.第七頁,共81頁。Part1MedicinalchemistryUnit1ProductionofDrugsThewholeconceptoftheproductionofdrugsTheclassificationofthedrugsTheintroductionofeachgroupofdrugs

第八頁,共81頁。Thefirstquestion:howtoclassifythedrugDependingonthekindsofdisease:CardiovasculardrugsDigestivesystemdrugsRespiratorysystemdrugsAntiviraldrugsProprietarydrugsorGenericdrugsDependingontheproductionororigin:第九頁,共81頁。藥品的生產(chǎn)依據(jù)其生產(chǎn)或來源,藥物制劑可以分為三類:I.完全的合成材料(人工合成材料),II.天然(tiānrán)產(chǎn)物,和III.源自部分合成的產(chǎn)品(半合成產(chǎn)品)。

Dependingontheirproductionororiginpharmaceuticalagentscanbesplitintothreegroups:I.Totallysyntheticmaterials(synthetics),II.Naturalproducts,andIII.Productsfrompartialsyntheses(semi-syntheticproducts).Unit1ProductsofDrugs第十頁,共81頁。Wordssyntheticsglycoside(s)hydrolysatedextrantargetedmodificationEpinephrineLevodopaProstaglandinsD-PenicillamineVincamineEukaryontProkaryontLeuconostocmesenteroidesCorynebacteriumglutamicumBrevibacteriumflavumPropionibacteriumshermaniipurinanucleotidecitricacidmonosodiumL-glutamatechromatinn.[用作復(fù)]人工合成(絕緣)材料n.配醣;配糖體;糖苷n.水解液;水解產(chǎn)物n.葡萄(pútáo)聚糖;右旋糖酐定向(或靶向)修飾n.腎上腺素n.[藥]左旋多巴(等于L-dopa)n.前列腺素(prostaglandin的復(fù)數(shù)形式)n.D-青霉胺n.長春胺n.真核細(xì)胞n.原核細(xì)胞腸膜狀明串珠菌谷氨酸棒桿菌黃色短桿菌謝氏丙酸桿菌嘌呤核苷(酸)檸檬酸谷氨酸鈉(味精)n.核染色質(zhì);核染質(zhì)第十一頁,共81頁。AlkalimetalLilithiumNasodiumKpotassiumRbrubidiumCscaesiumFrfranciumHhydrogen第十二頁,共81頁。本書的重點是在于Ⅰ和Ⅲ類中最重要的化合物——藥物合成。但是,這并不意味著,天然產(chǎn)品或其他制劑并不太重要。它們可以(kěyǐ)作為有價值的先導(dǎo)結(jié)構(gòu),他們常常作為重要的合成產(chǎn)品的起始原料或中間體產(chǎn)品。表1列出了獲取藥物制劑的不同方法的概述。

TheemphasisofthepresentbookisonthemostimportantcompoundsofgroupsIandⅢ-thusDrugsynthesis.Thisdoesnotmean,however,thatnaturalproductsorotheragentsarelessimportant.Theycanserveasvaluableleadstructures,andtheyarefrequentlyneededasstartingmaterialsorasintermediatesforimportantsyntheticproducts.Table1givesanoverviewofthedifferentmethodsforobtainingpharmaceuticalagents.第十三頁,共81頁。最初從天然資源庫獲得的幾個重要治療作用的天然產(chǎn)品,今天可以通過全合成更有效地,例如更經(jīng)濟地被制備(zhìbèi)出來。這樣的例子包括L-氨基酸、氯霉素、咖啡因、多巴胺、腎上腺素、左旋多巴、肽類激素、前列腺素、D-青霉胺、長春胺,以及幾乎所有的維生素。

Severaltherapeuticallysignificantnaturalproductswhichwereoriginallyobtainedfromnaturalsourcesaretodaymoreeffectively-i.e.moreeconomically-preparedbytotalsynthesis.SuchexamplesincludeL-aminoacids,Chloramphenicol,Caffeine,Dopamine,

Epinephrine,Levodopa,peptidehormones,Prostaglandins,D-Penicillamine,Vincamine,

andpracticallyallvitamins.第十四頁,共81頁。在過去的幾年里,發(fā)酵(fājiào),即微生物過程,變得極其重要。通過現(xiàn)代技術(shù)和基因選擇導(dǎo)致的微生物的高性能突異變種的結(jié)果,發(fā)酵(fājiào)已成為選擇寬范圍物質(zhì)的方法。真核細(xì)胞(酵母菌和霉菌)和原核細(xì)胞(單細(xì)胞細(xì)菌,放線菌)都可用作微生物??梢缘玫较铝挟a(chǎn)品類型:

Overthelastfewyearsfermentation-i.e.microbiologicalprocesseshasbecomeextremelyimportant.Throughmoderntechnologyandresultsfromgeneticselectionleadingtothecreationofhighperformancemutantsofmicroorganisms,fermentationhasalreadybecomethemethodofchoiceforawiderangeofsubstances.BothEukaryonts(yeastsandmoulds)andProkaryonts(singlebacterialcells,andactinomycetes)areusedmicroorganisms.Thefollowingproducttypescanbeobtained:

第十五頁,共81頁。盡管從諸如腸膜狀明串球菌的某些微生物的黏膜可以生產(chǎn)葡萄聚糖,但第2和3類產(chǎn)品類型只與藥品生產(chǎn)的有關(guān)。葡聚糖自身的分子量5萬?10萬,可用作血漿代用品。而來自谷氨酸棒桿菌和黃色短桿菌突變體的初級代謝產(chǎn)物中,L-氨基酸尤其令人感興趣。從這些生物體中,可以生產(chǎn)約35萬噸L-谷氨酸單鈉鹽(味精,食品添加劑)和約70,000噸L-賴氨酸(用于植物蛋白補充物質(zhì))。此外,重要的初級代謝產(chǎn)物還有嘌呤(piàolìng)核苷酸、有機酸、乳酸、檸檬酸和維生素,例如源自謝氏丙酸桿菌的維生素B12。

Disregardingtheproductionofdextranfromthemucousmembranesofcertainmicroorganisms,e.g.Leuconostocmesenteroides,classes2and3

are

therelevantonesforthepreparationofdrugs.Dextranitself,withamolecularweightof50,000~100,000,isusedasabloodplasmasubstitute.AmongtheprimarymetabolitestheL-aminoacidsfrommutantsofCorynebacteriumglutamicum

andBrevibacteriumflavum

areespeciallyinteresting.Fromtheseorganismssome350,000tonesofmonosodiumL-glutamate(foodadditive)andsome70,000tonesofL-lysine(supplementforvegetableproteins)areproduced.Furtherimportantprimarymetabolitesarethepurinanucleotides,organicacids,

lacticacid,citricacid,andvitamins,forexamplevitaminB12fromPropionibacteriumshermanii.第十六頁,共81頁。在次生代謝產(chǎn)物中首先必須提到的是抗生素。以下五組藥品代表了全球每年(měinián)價值170億美元:

青霉素類(產(chǎn)黃青霉),頭孢菌素類(頂頭孢霉菌),四環(huán)素類(金霉素鏈霉菌),紅霉素類(紅霉素鏈霉菌),氨基糖苷(如來自灰色鏈霉菌的鏈霉素)。

Amongthesecondarymetabolitestheantibioticsmustbementionedfirst.ThefollowingfivegroupsrepresentayearlyworldwidevalueofUS-$17billion:penicillins(Penicilliumchrysogenum),cephalosporins(Cephalosporiumacremonium),tetracyclines(Streptomycesaureofaciens),erythromycins(Streptomyceserythreus),aminoglycosides(e.g.streptomycinfromStreptomycesgriseus).第十七頁,共81頁。Dextranisapolymerofglucose.Itisawhitepowderanditissolubleinwaterandinsolubleinethanol.Dextrancanincreasetheplasmavolumeandmaintainthebloodpressure,soitcanbeusedforasabloodplasmasubstitute.Itcanbeproducedbyfermentationofsucroseinleuconostocmesenteroides.Certainly,thefermentationonlyproducetherawmaterialandthesomepurificationisnecessary.

ThesimpleintroductionofdextranMolecularformula:(C6H10O5)nglucose葡萄糖fructose果糖(guǒtáng)mono-,di-,tri-,polymer單體(dāntǐ),二聚體,三聚體,聚合體(物)sucrosen.蔗糖(zhètáng)第十八頁,共81頁。從微生物中已分離出約5000種抗生素,但其中只有不到100種有治療用途。但是,必須記住,許多衍生物已通過部分合成法來修飾以獲得治療用途;在過去的十年里,采用半合成方法(fāngfǎ)已從?-內(nèi)酰胺獲得了約50,000種制劑。發(fā)酵是在體積高達400m3的不銹鋼發(fā)酵罐中進行。為了避免受到噬菌體等微生物的污染,(發(fā)酵)全過程都必須在無菌條件下進行。由于更重要的是,發(fā)酵只在有氧條件下才能發(fā)生;因此,需要提供有足夠量的(無菌)氧氣或空氣。二氧化碳的來源包括糖類(碳水化合物),如廢糖漿、低聚糖類和葡萄糖。

About5000antibioticshavealreadybeenisolatedfrommicroorganisms,butoftheseonlysomewhatfewerthan100areintherapeuticuse.Itmustberemembered,however,thatmanyderivativeshavebeenmodifiedbypartialsynthesisfortherapeuticuse;some50,000agentshavebeensemisyntheticallyobtainedfrom?-lactamsaloneinthelastdecade.Fermentationsarecarriedoutinstainlesssteelfermentorswithvolumesupto400m3.Toavoidcontaminationofthemicroorganismswithphagesetc.thewholeprocesshastobeperformedundersterileconditions.Sincethemoreimportantfermentationsoccurexclusivelyunderaerobicconditions,agoodsupplyofoxygenorair(sterile)isneeded.Carbondioxidesourcesincludecarbohydrates,e.g.molasses,saccharides,andglucose.第十九頁,共81頁。Wordsammonium(ammonia)aminesodiumbicarbonatesodiumhydroxidehydrochloric/sulfuric/nitricacidhypochloritechloritechlorate

perchloratenitritenitratesulfidesulfitesulfate

persulfatephosphitehypophosphite

phosphatedihydrogenphosphatehydrogenphosphate銨;銨鹽(氨;氨水)胺碳酸氫鈉;小蘇打、NaHCO3氫氧化鈉、NaOH鹽酸;硫酸(liúsuān);硝酸次氯酸鹽(酯)亞氯酸鹽(酯)氯酸鹽(酯)高氯酸鹽(酯)亞硝酸鹽(酯)硝酸鹽(酯)硫化物;硫醚亞硫酸(liúsuān)鹽(酯)硫酸(liúsuān)鹽(酯)過硫酸(liúsuān)鹽(酯)亞磷酸鹽(酯)次磷酸鹽(酯)磷酸鹽(酯)磷酸二氫鹽磷酸一氫鹽第二十頁,共81頁。Prefix----------Parent-----------SuffixNomenclatureofparentpart:NomenclatureofalkanesandalkylsubstituentsStraight-chainalkanes

Straight-chainalkanesarenamedbycountingthenumberofcarbonatomsinthechainandaddingthefamilysuffix-ane.Thuspentaneisthefive-carbonalkane,andhexaneisthesix-carbonalkane.NomenclatureofOrganicCompounds1第二十一頁,共81頁。Analkylsubstituent(oranalkylgroup)isanalkanefromwhichasinglehydrogenhasbeenremoved.Alkylsubstituentsarenamedbyreplacingthe“ane”suffixofthealkanewith“yl”.Theletter“R”isusedtoindicateanyalkylgroup.ThusCH3-hasthenameofmethyl,whilethegroupofCH3CH2-wasnamedethyl.第二十二頁,共81頁。NumberMolecularNameNameinAlkylofcarbonsformulaChinesesubstituents1 CH4 Methane 甲烷 Methyl2 C2H6 Ethane 乙烷 Ethyl3 C3H8 Propane 丙烷 Propyl4 C4H10 Butane 丁烷 Butyl5 C5H12 Pentane 戊烷 Pentyl6 C6H14 Hexane 己烷 Hexyl7C7H16 Heptane 庚烷 Heptyl8 C8H18 Octane 辛烷 Octyl9 C9H20 Nonane 壬烷 Nonyl10 C10H22 Decane 癸烷 Decyl11 C11H24Undecane 十一(Shí-Yī)烷 Undecyl12 C12H26 Dodecane 十二烷 Dodecyl13 C13H28 Tridecane 十三烷 Tridecyl20 C20H42Icosane 二十烷 Icosyl21 C21H44Heneicosane 二十一(Shí-Yī)烷Heneicosyl30 C30H62 Triacontane 三十烷 Triacontyl第二十三頁,共81頁。Branched-chainalkanes3-ethyl-3-methylhexane第二十四頁,共81頁。SomeusefulprefixesforindicatingthenumberofsubstituentgroupsMono- 單取代(qǔdài),一取代(qǔdài)Di- 二取代(qǔdài)Tri- 三取代(qǔdài)Tetra- 四取代(qǔdài)Pent(a)- 五取代(qǔdài)Hex(a)- 六取代(qǔdài)Hept(a)- 七取代(qǔdài)Oct(a)- 八取代(qǔdài)Nona- 九取代(qǔdài)Deca- 十取代(qǔdài)2,6-dimethyloctanenot2-ethyl-6-methylheptane3-ethyl-2-methylhexanenot3-isopropylhexane第二十五頁,共81頁。Someusefulprefixesusedtonamebranchedalkanes(Commonnames)(normal)n- 正(isomer)iso- 異neo- 新primary 伯,一級(secondary)sec-仲,二級(tertiary)tert- 叔,三級quaternary 季,四級

n-pentaneneopentaneisobutane正戊烷新戊烷異丁烷

Pentane2,2-dimethylpropane2-methylpropanetert-butanoliso-butanamine

sec-butanamine叔丁醇異丁胺仲丁胺2-methyl-2-propanol2-methylpropanamine1-methylpropanamine第二十六頁,共81頁。

Theunivalentradicalderivedfromacyclicalkeneoralkynehastheendings“-enyl”or“-ynyl”,(alkenealkenyl)(alkynealkynyl),andthepositionofthedoubleortriplebondisindicatedwherenecessary.(unlikealkanealkyl)e.g.

1-propenyl2-butenyl

ethynyl2-propynyl第二十七頁,共81頁。Thefollowingnon-systematicnamesareretainedEthylene(乙烯)Allene(丙二烯)Acetylene(乙炔(yǐquē))Isoprene(異戊二烯)Vinyl(乙烯基)Allyl(烯丙基)Isopropenyl(異丙烯基)第二十八頁,共81頁。NomenclatureofacyclichydrocarbonswithtwoormoredoubleortriplebondsTwoormoredoublebonds:theendingwillbe“-adiene”,“-atriene”etc.(alkadiene)Twoormoretriplebonds:theendingwillbe“-adiyne”,“-atriyne”etc.(alkadiyne)e.g.

2-methyl-1,3-butadienepropadiene2,5-dimethyl-2,4,6-octatriene

3-ethyl-4-methyl-1,6-heptadiyne第二十九頁,共81頁。Nomenclatureofmonocyclicaromatichydrocarbons苯甲苯二甲苯苯乙烯異丙苯均三甲苯benzenetoluenexylenestyrenecumenemesitylene苯基(běnjī)甲苯基(běnjī)二甲苯基(běnjī)苯乙烯基異丙苯基(běnjī)均三甲苯基(běnjī)芐基Phenyltolylxylylstyrylcumenylmesitylbenzyl第三十頁,共81頁。Commonnamesretainedforthedisubstitutedbenzeneortho-,o- 鄰meta-,m- 間para-,p- 對

m-methylbenzylm-tolyl3,4-dimethylphenyl3-methylbenzyl

3-tolyl

o-styrylp-cumenyl3,5-dimethyl-4-ethylphenyl

2-styryl4-cumenyl

第三十一頁,共81頁。SomeimportantFamiliesoforganicmoleculesSaturatedhydrocarbons:suchas:Alkanes;cycloalkanes;Un-saturatedhydrocarbons:suchas:alkenes;alkynes;cycloalkenes;cycloalkynes;cycloalkadienes;cycloalkadiynes;Aromaticcompouds:benzene;biphenyl;naphthaleneandotherfusedandpolycyclicaromatichydrocarbons;Compoundswithfunctionalgroups:alkylhalides(鹵代烴);alcohols(醇);phenols(酚);ethers(醚);amines(胺);Compoundswithfunctionalgroups:aldehydes(醛);ketones(酮);quinones(醌);carboxylicacids(羧酸(suōsuān));esters(酯);acylhalides(酰鹵);acidanhydrides(酸酐)amides(酰胺);imides(亞胺);第三十二頁,共81頁。Compoundswithfunctionalgroups:

alkylhalides(鹵代烴);alcohols(醇);phenols(酚);ethers(醚);amines(胺)etc.alkylhalides R-X halogen(-halo)(-Cl,-Br,-F,-I)Alcohols R-OH hydroxygroup(-OH)Phenols Ar-OH hydroxygroup(-OH)Ethers R-O-R’ Alkoxygroup(O-R’)Amines R-NH2 aminogroup(NH2)第三十三頁,共81頁。

Alkylhalides(haloalkaneoralkyl

halide)Alkylhalidesareclassifiedasprimary,secondary,ortertiarydependingonthecarbontowhichthehalogenisattached.第三十四頁,共81頁。

Thecommonnamesofthealkylhalidesareobtainedbycitingthenameofthealkylgroupfollowedbythenameofthehalogen.(alkyl

halide)

IntheIUPACsystem,alkylhalidesarenamedassubstitutedalkanes.Thesubstitutedprefixnamesforthehalogensendin“o”(fluoro,chloro,bromo,iodo).(haloalkane)第三十五頁,共81頁。Alcohols

Thecommonnames,similartoalkylhalides,areobtainedbycitingthenameofthealkylgrouptowhichtheOHgroupisattached,followedbytheword“alcohol”.(alkyl

alcohol)

TheIUPACnameforanalcoholisobtainedbyremovingthe“e”fromthenameofthealkaneandaddingthesuffix“ol”.(alkanol)Nomenclatureofalcohols第三十六頁,共81頁。Aminesarecompoundsinwhichoneormorehydrogenofammoniahavebeenreplacedbyalkylgroups.Thereareprimary,secondary,andtertiaryamines.Thisclassificationdependsonhowmanyalkylgroupsarebondedtothenitrogen.

(!!!notcarbon)Nomenclatureofamines第三十七頁,共81頁。Thecommonnameofaamineisobtainedbycitingthenamesofthealkylgroupsbondedtothenitrogeninalphabeticalorder.Theentirenameiswrittenasoneword.

(alkylamine)e.g.第三十八頁,共81頁。TherearetwoIUPACapprovedwaytonameanamine.Itcanbenamedasasubstitutedalkaneusingtheprefix“amino”todesignatetheaminesubstituent.(???aminoalkane)Italsocanbeennamedwithafunctionalgroupsuffix----“amine”.The“e”attheendofthealkanenameisreplacedby“amine”.ThenamesofsubstituentsbondedtothenitrogenareprecededbyanN

(initalic)toindicatethatthesubstituentisbondedtoanitrogenratherthantoacarbon.[(N-alkyl)alkanamine]第三十九頁,共81頁。第四十頁,共81頁。Amineswithfouralkylgroupsbondedtothenitrogen-andthereforeapositivechargeonthenitrogen-arecalledquaternaryammonium

salts.Theirnamesareobtainedbycitingthenamesofthealkylgroupsinalphabeticalorderasaprefixto“ammonium”,followedbythenameofthe

counterion.

[alkylammoniumhalide

(orhydroxideetc)]第四十一頁,共81頁。Nomenclatureofetherssymmetricaletherandasymmetricalether.e.g.第四十二頁,共81頁。Thecommonnameofanetherisobtainedbycitingthenamesofthetwoalkylsubstituents(inalphabeticalorder)followedbytheword“ether”.Thesmallestethersarealmostalwaysnamedbytheircommonnames.(alkylalkyl

ether)

TheIUPACsystemnamesanetherasanalkanethatbearsanalkoxysubstituent.Alkoxysubstituentsarenamedbyremovingthe“yl”fromthenameofthealkylsubstituentandadding“oxy”.(alkoxyalkane)methoxyethoxy1-methylethoxy1,1-dimethylpropoxy第四十三頁,共81頁。Acarbonylgroup(羰基(tānɡjī))isacarbondoublybondedtoanoxygenandanacylgroup(?;﹊sacarbonylgroupattachedtoanalkylsubstituent.Abenzoylgroup(苯甲?;﹊sacarbonylgroupattachedtoabenzenering.第四十四頁,共81頁。Thecommonnameofanaldehydeisthesameascarboxylicacid(derivedfromsomeLatinwords).(Latin+aldehyde)TheIUPACnameofanaldehydeisobtainedbyremovingthe“e”fromthealkanenameandadding“-al”.(alkanal)Nomenclatureofaldehydesandketones第四十五頁,共81頁。Ifthealdehydegroupisattachedtoaring,thealdehydeisnamedbyadding“carbaldehyde”tothenameofthering.(cycloalkanecarbaldehyde)phenylmethanal第四十六頁,共81頁。Commonname:Onlyafewketonshavecommonnames,suchasacetone(likealdehyde).Commonnamesarealsousedforphenyl-substitutedketones.Theyarecalledphenones.(+one)IUPACname:KetonesarenamedintheIUPACsystembyremovingthe“e”fromthealkanenameandadding“-one”.(alkanone)Derivedname:Likeethers,R-CO-R’canbenamedbycitingthenamesofthetwoalkylsubstituents(inalphabeticalorder)followedbytheword“ketone”.(alkylalkyl

ketone)Nomenclatureofketones第四十七頁,共81頁。CommonnameIUPACnameDerivedname第四十八頁,共81頁。NomenclatureofcarboxylicacidsanditsderivativesX=OH,acarboxylicacidX=halogen,anacylhalideX=OR',anesterX=OCOR',anacidanhydrideX=NRR',anamide第四十九頁,共81頁。Nomenclatureofcarboxylicacids

acarboxylgroup

Thefunctionalgroupofacarboxylicacidiscalledacarboxylgroup.Long-chaincarboxylicacidsarecalled“fattyacids”.

第五十頁,共81頁。Commonname:Carboxylicacids(<6)arefrequentlycalledbytheircommonnames.Theyarenamedbyadding“Latinprefix”before“acid”.?whatisα–carbon?

IUPACname:acarboxylicacidisnamedbyreplaceingthe“e”endingofthealkanenamewith“–oicacid”.(alkanoic

acid)Carboxylicacidsinwhichacarboxylgroupisattachedtoacycliccompoundcanbenamedbyadding“carboxylicacid”tothenameofthecycliccompound.第五十一頁,共81頁。benzoicacid第五十二頁,共81頁。NomenclatureofacylhalidesAcylhalidesarenamedbyusingtheacidnameandreplacingthe“–icacid”with“–ylhalide”(alkanoyl

halide),orbyreplacing“carboxylicacid

”with“carbonylhalide”(cycloalkanecarbonylhalide)第五十三頁,共81頁。benzoylchloride第五十四頁,共81頁。Nomenclatureofacidanhydrides?Doyouknowthemeaningof“anhydride”

R=R’,asymmetricalanhydride

R≠R’,amixedanhydride第五十五頁,共81頁。Symmetricalanhydridesarenamedbyusingtheacidnameandreplacing“acid”with“anhydride”,mixedanhydridesarenamedbystatingthenameofbothacidgroupsinalphabeticalorderfollowedby“anhydride”.第五十六頁,共81頁。Innaminganester,thenameofthegroupattachedtothe“carboxyloxygen”isstatedfirst.Thisisfollowedbythenameoftheacidwith“-icacid”replacedby“-ate”.Saltsofcarboxylicacidsarenamedinthesameway.

(R’alkyl

R

alkanoate)Nomenclatureofesters第五十七頁,共81頁。ethylacetate第五十八頁,共81頁。

AprimaryamideasecondaryamideatertiaryamideAmidesarenamedbyusingtheacidname,replacing“–oicacid”or“-icacid”with“amide”,orbyreplacing“carboxylicacid”with“carboxamide”.(alkanamide)or(cycloalkanecarboxamide)Nomenclatureofamides第五十九頁,共81頁。第六十頁,共81頁。NomenclatureofnitrilesIncommonnomenclature,nitrilesarenamedbyreplacing“–icacid”with“-onitrile”,ortheyarenamedas“alkyl

cyanide”.(alkyl

cyanide)InIUPACnomenclature,nitrilesarenamedbyadding“-nitrile”tothealkanename.(alkanenitrile)第六十一頁,共81頁。Alkalineearths(堿土(jiǎntǔ))Magnesium(鎂)Calcium(鈣)Aluminum

(鋁)Tin

(錫)Lead

(鉛)第六十二頁,共81頁。TransitionMetals:Titanium(鈦)Chromium(鉻)Manganese(錳)Iron(鐵)Cobalt(鈷)Nickle(鎳)Copper(銅)Zinc(鋅)Silver(銀)Platinum(鉑)Gold(金)Palladium(鈀)第六十三頁,共81頁。另外必須提供微生物的生長介質(zhì)必須含有諸如硫酸銨、氨水或尿素等含氮化合物,以及無機磷酸鹽。此外,必需有的恒定的最佳的pH值和溫度。以青霉素G為例,發(fā)酵過程在200小時后完成,細(xì)胞團塊經(jīng)過濾(guòl(fā)ǜ)而分離。從濾液中經(jīng)吸收或提取工藝而分離出所需要的活性制劑。細(xì)胞團塊,如果并非目的產(chǎn)品,由于其高蛋白質(zhì)含量,可進一步用作動物飼料。

Additionallythemicroorganismsmustbesuppliedinthegrowthmediumwithnitrogen-containingcompoundssuchasammonium

sulfate,ammonia,orurea,aswellaswithinorganicphosphates.Furthermore,constantoptimalpHandtemperaturearerequired.InthecaseofpenicillinG,thefermentationisfinishedafter200hours,andthecellmassisseparatedbyfiltration.Thedesiredactiveagentsareisolatedfromthefiltratebyabsorptionorextractionprocesses.Thecellmass,ifnotthedesiredproduct,canbefurtherusedasananimalfeedstuffowingtoitshighproteincontent.第六十四頁,共81頁。利用現(xiàn)代重組技術(shù),已獲得的微生物可以生產(chǎn)(shēngchǎn)原始基因中并未編碼的多肽。修飾過的大腸桿菌使得產(chǎn)生人類胰島素或前胰島素原類似物的A-和B-鏈成為可能。經(jīng)分離后再選擇性形成二硫鍵,其最終提純由色析(譜)工序來決定。通過這種方式,完全可以不受限制地從任意的動物胰腺原料獲得人類胰島素。

Bymodernrecombinanttechniquesmicroorganismshavebeenobtainedwhichalsoallowproductionofpeptideswhichwerenotencodedintheoriginalgenes.ModifiedE.colibacteriamakeitthuspossibletoproduceA-andB-chainsofhumaninsulinorproinsulinanalogs.Thedisulfidebridgesareformedselectivelyafterisolation,andthefinalpurificationiseffectedbychromatographicprocedures.Inthiswayhumaninsulinisobtainedtotallyindependentlyfromanypancreaticmaterialtakenfromanimals.第六十五頁,共81頁。其他(qítā)重要的肽,激素和酶,如人類生長激素(HGH),神經(jīng)活性肽,生長抑素,干擾素,組織型纖溶酶原激活劑(TPA),淋巴因子,如鈣調(diào)蛋白的鈣調(diào)節(jié)劑,蛋白疫苗,以及作為診斷用單克隆抗體,也是應(yīng)用這種方法合成的。

Otherimportantpeptides,hormones,andenzymes,suchashumangrowthhormone(HGH),neuroactivepeptides,somatostatin,interferons,tissueplasminogenactivator(TPA),lymphokines,calciumregulatorslikecalmodulin,proteinvaccines,aswellasmonoclonalantibodiesusedasdiagnostics,aresynthesizedinthisway.第六十六頁,共81頁。一個單一的微生物中所存在的酶或酶系統(tǒng),可應(yīng)用于控制的立體定向的和位置定向的化學(xué)反應(yīng)。這個原理在類固醇化學(xué)尤其有用。在這里,我們只能提及黃體酮經(jīng)微生物法的11-α-位羥基化反應(yīng)制得11-α-羥基黃體酮,一個用于合成可的松(腎上腺皮質(zhì)酮)的關(guān)鍵產(chǎn)品。今天(jīntiān),分離出的酶很重要,不僅因為淀粉的酶法糖化技術(shù)的重要性以及葡萄糖異構(gòu)化成果糖,而且它們在用于診斷疾病的無數(shù)檢測程序和用于監(jiān)測治療的酶法分析中也很重要。

Theenzymesorenzymaticsystemswhicharepresentinasinglemicroorganismcanbeusedfordirectedstereospecificandregiospecificchemicalreactions.Thisprincipleisespeciallyusefulinsteroidchemistry.Herewemayreferonlytothemicrobiological11-α-hydroxylationofprogesteroneto11-α-hydroxyprogesterone,akeyproductusedinthesynthesisofcortisone.Isolatedenzymesareimportanttodaynotonlybecauseofthetechnicalimportanceoftheenzymaticsaccharificationofstarch,andtheisomerizationofglucosetofructose,Theyarealsosignificantinthecountlesstestproceduresusedindiagnosingillness,andinenzymaticanalysiswhichisusedinthemonitoringoftherapy.第六十七頁,共81頁。大量的酶本身可以作為活性成分。因此,含有蛋白酶(如糜蛋白酶,胃蛋白酶和胰蛋白酶),淀粉酶和脂肪酶的制劑產(chǎn)品,大多與合成的抗酸藥相配合,以促進(cùjìn)消化。鏈激酶和尿激酶是重要的溶血栓劑,而天冬酰胺酶則用作治療白血病中的細(xì)胞生長抑劑。

Anumberofenzymesarethemselvesusedasactiveingredients.Thuspreparationscontainingproteases(e.g.chymotrypsin,pepsin,andtrypsin),amylasesandlipases,

mostlyincombinationwithsyntheticantacids,promotedigestion.Streptokinaseandurokinaseareimportantinthrombolytics,andasparaginaseisusedasacytostaticagentinthetreatmentofleukemia.第六十八頁,共81頁。最后必須提到的是,酶作為生物催化劑在化學(xué)反應(yīng)的重要應(yīng)用,其中立體專一性和選擇性可以得到應(yīng)用。著名例子有酶裂解N-乙?;?D,L-氨基酸的外消旋體而生成L-氨基酸,從芐基青霉素經(jīng)青霉素酰胺酶作用生產(chǎn)8-氨基青霉烷酸,以及天門冬氨酸酶催化氨對富馬酸立體專一性加成反應(yīng)以生產(chǎn)L-天門冬氨酸。在這些應(yīng)用中,酶可以固載的形式(xíngshì)—某種方式連接在載體上—使用,也可以雜相催化劑的形式(xíngshì)來使用。這是有利的,因為它們可以很容易從反應(yīng)介質(zhì)中分離,并回收再利用。

Finallymentionmustbemadeoftheimportantuseofenzymesas‘biocatalysts’inchemicalreactionswheretheirstereospecificityandselectivitycanbeused.KnownexamplesaretheenzymaticcleavageofracematesofN-acetyl-D,L-aminoacidstogiveL-aminoacids,

theproductionof8-aminopenicillanicacidfrombenzylpenicillinbymeansofpenicillinamidaseandtheaspartase-catalysedstereospecificadditionofammoniatofumaricacidinordertoproduceL-asparticacid.Intheseapplicationstheenzymescanbeusedinimmobilizedforms-somehowboundtocarriers-andsousedasheterogeneouscatalysts.Thisisadvantageousbecausetheycantheneasilybeseparatedfromthereactionmediumandrecycledforfurtheruse.第六十九頁,共81頁。benzylpenicillinAminopenicillanicacidpenicillinamidaseFumaricacidaspartaseL-asparticacid第七十頁,共81頁。另一個基于蛋白酶專一性作用的重要工藝是應(yīng)用于半合成人胰島素

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