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06 Summary.Pdf SPPflX th1. 'h•• l. la a~out the appl1oatloa ot high-p.rtoraaao. 11quid ohroaatograplq (HPLO) '0 aoa. ape.ltlo real-11t••• paratl_ ani quant1t.tlon pro~l ••a regar41ng c.rtala 1acluatr1all7 ua.tul organ10 ,rodua'•• JI.mAl-paa•• adsorp'loa (.1110. ,el) and reTerad-pha •• partl tlOll (ltcm4" ph.1l11) ao4e. ot BPLO wer. ..plo," lD. tM • • tud,. Bo'h laooratle &D4 Iradl'" .lution .ode. were u." tor the ••paratlona an4 quantltatlOD.. th. suoc.sstul .imultan.ou. s.par.'lona laolud. seTeral altalo14s 1a sua oplua extrao'., aea1-a,.th.tl0 cod.ln. b ••• and lts llk.17 oarr,J over and .,nth.al. b7-produot t.purltl •• , 1-naphthllaa1n. fro. 2-naphth71aata. and other .truotural17 related lapur1tl••• an4 2-phen71gl101n. and 1 t. B-oarbaJllo,l- and h7d&lltoU preouraora. the ext.mal standard quantlta'1oa work laTolv•••• s&7 ot .ea1-a1Jl'h.ti0 codeill. bas. and anal ,sl. of the t1T. pr1llo1,al alltalolcla 1n gull op1ua, 'h. 2-1... er in bulk 1-aaphtb¥laa1n• ...pl.. (ault-p,. le.,..1) J th. \vo ao.t lU.l.T b7-produo' lal'uritl •• la .ea1-aJllth.tl0 oocl.lD.. base J aDd ~ (-)-2-pbeqlgl701ne . 'd. 'U1 It. -.carbaao71- aad hTdantola precursors 1n microbial traD.to~ a'loa reao'loa aix'urea. the t he sl. 1. dlTlded tato tour ohapters and t he ~l r8 ' o~ter 1& subdlvlded into tvo S. c tlOA~. The highlights of t h. vork in eaoh ohapter 1. d •• erlb.e4 1D. this BUA1Dla17. Til gltng-I ISOORAfIO BIGB-1ElJOBKAlOJ LIQUID gBROJUfOGJUlHI 0' GUll OPIUII ~1Jl,OIDS O. J. BOBDED PHDn SfJ.'lI01U.RY PBASE Seot1on .t. Siaul tanecua Separation ot the Principal .Alkaloids 1a Gu. Opiua 'I aeTersed-lha.e B1&h-pertoraan.e Liquid Olu'oaatography U.1ng a pH 11 btll!er Reversed-phaae BPLO on banded stat1on&r7 phase. ot TariO•• polarltles 1. a popular a04e tor aeparating princ1pal alkalold. ln sua aplua. Mo.t ot the ohroaatosrapber. haTe .a.. elther expenslTe aoetonltrile aloae or ln ooab1natlon with 10a-palr1D& reasent. d the aobl1e phase aodlt1en to aohieTe a slllultalleft. Howeyer, .e aohleyed a almultaneou. 'a•• lln. aeparatlon ot all tbe pr1D.o1pal alkalolda (aorphine. oocleU.. the b ain. • Ilo.oapu. anel papayerla.) 1n Iacllan sua oplUli .nraot. on a reTer.eel-pha•• bonded ph..,l ooluan with a sl.ple aDd taexp.nalYe,but n.gleoted, a.thaaol--1%(w/T)aqu.oua aodlum aoetat. and 7aM trlethllamiae (pH 11) butter (58,42) w.a used aa the aobl1. pbaae. A 100d p.at ar-et17 tor all the p.aka waa obaen" with UV 4et.otl_ at 254 u. fh. high perc.ntage ot .ethaaol appears to bay. aoae prote.tlye tan... ce on the al110a backbone ot the paoklq at the hlgh apparent pH. HoweTer. tor extendiDg tbe llt. ot the aala oolusa a 81110a presaturator oolwm ls reooaa.ad.~ viil Olm"I ISOOIAfIO HIGB-PBllfOIMJJOB LlQUD OBROJUtOQB.OBY 0' GUll OlIO IJ,lALOIDS OW A BODD PDI!L St.l!IOIABt lBASI Seo'loa B _ • .,. aDd .&aal,.18 .f • ..s..a,.'.. "10 004.1JM 1aII. ~ 18.. ra'10 a.TeraN-IJlaa. B1p.p.rtoaaao. Llqa14 ~~Iq 004.b.. 1. pbaraa••• U.oal.l, \he a.a' 1apon.a, .... Uae sua opl_ alkaloi4s with "1"14 p""",,loa Yo1_e fta.ldol 200 " .. alialold. ..lag . a1afW (oa.- t '0 . $ w/-) 0_'1'"u' of pa op1_. aoat. .f the, .... ta. pr04uCM4 ....1'.18117 1. dert... .01- .7Il~U.al17 ., £ ....~1.'1_ .f aorphi... On. ....... raw ••".rlel fer the ....faotv • • f .04.la., SeII1-retlae. aoJlph1ae ( •••q. 85~ -/w) 1. ".-..117 o"'aIIlaaM4 with ...0Al ••el •• ani" "".1' tJ'_ _ op1_ .\In.zaa 1ao1.'1on ,roc •••• Ia 'Ma ••n1_ w. ",on & 81aul t._.oa ••para'loa ot ••al­ .7JltAet.l. oodal.. , ... .troa \he 1IIU'...... aOJ'phine aIl4 ...ea1o f~~ _ 6 &014, .. well .. 'U4I t.YO GO_ .1Jl~.la '7-pr04uo:ta, ....1" i - Godaa. ..'_1 et.Jaer u4 cx .....1a.t.ht... oalU. P~Y101l817 n- ,oned BPLO .ath04 •• we ..e4 • , ..... ph..,l ••1_ aa4 • alap1• .. la.zpa..l_ ..tbeDol.-. q...... 1 11M ,rs..tbl1__ 1\11l pboaplaa'. 'utter at p H 3.0 (20180) .... 1 ...ratl0 aobU. pha•• fer the _., aa4 ..a1781. .f .u1-a,.'Mt.l0 00481a. b_. !'* p.ak are. reapoa... .~ 254 a. .t•• ~loa ••Teleact.h ••re l1a.ed ., 1 ..., ap ,. 100 )IS oodeta. eD4 10 )lg eaob tor \he tvo b1-product impurities in 25-~ injection volume. The method vas tound to be suitable tor monitoring the progress of the methylation react10n and also to assess the qual1t1 ot code1ne produced. QI APt ER-I I (lUDI.t UTERSBD-PlUS:B BIGH-PERlOlUUBOE LIQUID OHROJlJ.!OGR.&lBlO SEfJ.lU!IOB O}' mGB! ALKALOIDS AID MEOONIO AOID AID QUAlTI!A!IOB 01 fiVE PRINCIPAL ALKALOIDS IIi GUK OPIUll Re v~ rs ed-pha.e 1.coratlc BPLO on bonded statian&r,1 phaae. with di ffer ent polaritle. 1. a frequantl1 used method tor separation and quantitation ot gua opiua alkaloid,. Hovever, a coamon draw­ back ot 80me ot the earlier .ethods using th1s lI04e 1. that a h1ghl1 polar morphine elute. ahead ot other principal alkalold. OR the tailing edge ot the earl1 eluting group ot peak. represent­ ing polJaerio and polar constituent.. In this situation a rellable lntegration ot the .orphine peat 1. difficult. fUrther, several chroaatographer. have reported low effectlveness ot reversed-phase colUllJls 1D. lsooratlc .ode tor basic compounds. In order to overoo.e these l1mitations, we used gradient elutlon 1n the present work. PreT1oual1, reversed-phase gradient elution lIode va8 applled to this separation problem with onl1 limited success. the separation of the tive princlpal alkaloids (llorphine, oodeine, thebaine, n08capiRe and papaverine), three minor alkaloid. (laudanosiRe, or,rptopine and naroeiRe), meconlc acid and so.e un­ identlfied constituents In gum oplum was achleved on a reversed­ pbase phenrl oolumn b7 gradlent BPLO using a slmple and inexpensive .obile phase s1stem. The llnear gradlent programae was started x a' 5~ .... eaded a~ 7Q%(y/y) ••thallol 1D 1 IlH tr1.~h11 ...aa1_ pllo.phat. butfer (pH ') 1a 20 aiD. jll the t1Ye pr1Dolpal alkaloid. vere al.o 4.tera1ne4 w1 ~ 800d preolaloa. the .ethod req111n. -1111_. • ..ple preparat1i1l aD4 18 au ~abl. tor 1'OU,s.ae 91 t "U-III SU.AJU.!IOlif 01 1-.J,PBfJlU,AIIlJlB 1R01l !HI nn; DOd IJIPUBItIBS AJlD SUB-JPK I,fiEt DEfEOflOI .&lID Qt1.D!Il'J.fIOK 0' 2-IUIllHILAMI.E BY BODAL !H.&S~ BIGB-PlaIOBJU.lO! LIQUID OIlROll..l!OGlUPBI the tree baa. 1-Aaphtlqlaa1ne and c.r~a1n of it. aulphOD.1o acid 4eriYatlY••• 8n ... 41aso aU cOl1pl1Ag oOllp_eat. ill the preparatia of asO 41•• which lAol,," •• ao.e perm1 tt" s1llth.~10 food coloun. 'fecba1cal '....,h\lql.. 1a. 1a \18"81 17 produoe4 b1 reclllOtl_ .t 1-aS. traaaphthal.n. whioh 1 ~s.lt 111 1JlYariabll ooata­ II1aat.4 with the 2-111 tre- ls_er. fh. teohnioal 1-aaph\hTl.a1n• • 87 o_'alll s ..e 1.1'-41napbtb71aa1ae. 1.5-d1ea1noaaphthal... e. 1- m4 2-aapllthole aB4 lllYaria'17 a little of tb. 2-1aoaer (.u. 0.5% wi") .a 1apu.r1tie.. !h. 2-Dapht}qlaa1Jle bas 10Dg b... 1'8- as oogal.ed .. a Alman caro1Jlogen aadL a tonc ohemioal. It. a.lI- faoture .ad " •• 1. IlOV baDlle4 all OYer the vOl'ltt. It h8e been aotuall, touad to be pna_t 111 a._ l-naphtb71ftll1De ba'H~d aSO a11l'the'10 food ooloura, .oat probab17 aa a Oa:rq 9vttr upur1"7. ID thl. a.otion a BPLO .ethod 1e reported for ~ 81aal'aaeou8 'a.elin••• para'laD ot 1-llaph'h71aatae and th. five assoclat•• iapur1,\le•• 1l8lle17. 2-JlapbthTlaa1De. 1.5-dl.... 1.Ollapl1thaleD. •• t.l'-41JlaphtbTlaa1De. 1- and. 2-naphthol. u8lng l i quid-solid ".orp~lQR mode aa a .1110. sel .,.tlaaarr phaa.. fhe ••bl1e phaae ... 50~ .a~.r--.aturate4 filet-bTl .ther-li-hex.. e (25.15). fh. lIeth04 &._1e4 preol.. cl.'.l'II1aatloa ot trao. ,,0_"_ of 2-naphtbllaa1ne lmpurl '7 1.D ~.obld.oa1 1-aaph~1aa1Jl.... pl •• ChI1ag t.o a hlgh d.egre. ot r.aol\l~loJl (b = 2.5) ao111 ...ed. ...~ .. _ these .truotural laOll.n.. fhe ••t1aatecl alal-_ ,.t•• table ..._, JI'\. ot a-aaphthl1d1DeLa_ 1500 pp. a-hexaa•• 01.tl_ ot 1-aapthfl- aai•• 1. lI- 0.06 ppaCw/w)aD.C1 'b.a~ 1a bulk t-aapll'b71aalae 1. S- O.OO4~ (./.~" the low r 11m! t 0911 lie i Dlp reyed tt.lnller y.~ ...11,. CIM1Ill=U lIO:lItOBI.lG 0 .. SfBUOtlRBOlnO HIOBOBIAL fUlSlOlUlltIOB 0' J}lt-5-J-iIDllJaDAftOL'I fO i(-)-2-PBBIl'LGLIOIllB .BY ISoOlUfIO UYERSD-:raUUI HI GB-P.IUOmt4I'OB LI QUID OBRO}UfOCJ!UPHI j.(-)-2-phQTlg17c1ne 1 ... 1aporlallt etan1D& ..,.rial tor produolDs .ea1-.1Dthetl0 )l-l•• t_ aatlblotloa ...h .. pea10111laa aDd o.phal•• portRa. .... tloaer1oal17 pure ~(-)-2-ph..,1&l701a. OaB be prepared hI esplo7in& atereoapeolJ1o ea~.'l. traa.toraatlaa of PJt.-5-phu71bTdanto111 Tia the l-(-)-N-oarbam071-a-phe..,1sl70 1.. laterae41at. u1Dg baot.ria ••oh aa w0l!aot.X'1ua aacl , ••••••• ap.cl... A ...r y 1mponan't, ad.,an't,age of bldant.o1aa 1ii 'beir t ...l1. aD4 epontan.oua chem10al raoe.tz&t1aa even under all' o ~.810 oatall.is oonditions ( •• s., pH 8.5; temp. JO 0). Thu., .. • re8ul" o~ onenoal raoell1zatlel1 of the a reaot1v•• (+)-5-pbelql­ b1dan~ola and s1multan.ous ater.osele.ilv. m1oro~lal hl4rolJal. ~1 ~tqdaDto11la". R,k-5-Ph'B71Q4aat.1a 1.
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