Choughuley, Ahmed S.U.

Lemmon, Richard M.

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Lawrence Berkeley National LaboratoryRecent WorkTitlePRODUCTION OF CYSTEIC ACID, TAURINE, AND CYSTAMINE UNDER PRIMITIVE EARTH CONDITIONSPermalinkhttps://escholarship.org/uc/item/3np312fnAuthorsChoughuley, Ahmed S.U.Lemmon, Richard M.Publication Date1965-11-30eScholarship.org Powered by the California Digital LibraryUniversity of CaliforniaUCRL-16572 University of California Ernest 0. Radiation lawrence Laboratory PRODUCTION OF CYSTEIC ACID, TAURINE, AND CYSTAMINE UNDER PRIMITIVE EARTH CONDITIONS TWO-WEEK LOAN COPY This is a library Circulating Copy which may be borrowed for two weeks. For a personal retention copy, call Tech. Info. Division, Ext. 5545 DISCLAIMER This document was prepared as an account of work sponsored by the United States Government. While this document is believed to contain correct information, neither the United States Government nor any agency thereof, nor the Regents of the University of California, nor any of their employees, makes any warranty, express or implied, or assumes any legal responsibility for the accuracy, completeness, or usefulness of any information, apparatus, product, or process disclosed, or represents that its use would not infringe privately owned rights. Reference herein to any specific commercial product, process, or service by its trade name, trademark, manufacturer, or otherwise, does not necessarily constitute or imply its endorsement, recommendation, or favoring by the United States Government or any agency thereof, or the Regents of the University of California. The views and opinions of authors expressed herein do not necessarily state or reflect those of the United States Government or any agency thereof or the Regents of the University of California. · . . .. . '. Submitted to Nature UNIVERSITY OF CALIFORNIA Lawrence Radiation Laboratory Berkeley, California AEC Contract No. W-7405-eng-48 UCRL-16572 " PRODUCTION OF CYSTEIC ACID, TAURINE, AND CYSTAMINE UNDER PRIMITIVE EARTH CONDITIONS Ahmed S. U. Choughuley and Richard M. Lemmon November 30, 1965 .. -~ ~ . ·\ ''.·' .. ' ~ ..... " .. ,· •. ,· ' ··'\-. ,. ' :·" \ I,..~ t • I'~ •0' .I . , ·. ' • • .~ .. .. ..•. ·=., . ·. . ~ .. · ..... ~4·· ...... ·~ · .. ... ' . ~· . ·,;·. ; ·. ~ ·:. PRODUC'J'Im; OF' CYSJ''EIC ACID, TATJRilm, MID CYm'Ar.U:f'S UNDER PRIMITIVE EARTH COi-!DITIONS . .,. It ir. nm1 M?ll entnbl1:-Jhet1 that moat of the s~le, h1olog!cally-ir:iportGnt "r..onor:.ern" (r.uoh 1!.!l er.:ino ao1dB, pentOBeS1 purines, and fatty Hcidn) are fomcd \·lr~cn vnr1cuR h1p;h ~ne~.3' Gources are applied to samples of the primitive Earth'G atmoGphere1,2, '.i'h1s atT"Dnphere 1B asfl\.U'IlC6 to ' . COl"lBist mainl:~ (;f CHll• l/20• ~lH3• u2 o.na n2 (too last decrcos1ng rapidly \·dth jncr.ensc-d aec or the carth)3. Although thG run1no oo1dA are among the- r:-Dst prom1ncnt prodUCtS Of the 1rrad1at1ono Of "primitive-Earth o.t:-:nr;nhcrc:J •" no repol"t has y~t appca.n-!d 1n tho l1teraturo or the appc:arnnce of the r.ulphlL--conta1n1ne; ~.mino acid a • This hno prene.nted no pro~le-m, since tt can ·oo aafely oo:nJr.lCd that the primitive atmoophere • ccntaincd at len~t traces of H2!",_ho~er; 1t 1B o.l~s $IOCX1 to have la.boratory exper:iJJ);)ntat1on to hnck UD asmm1pt1ons. · . ' Primitive-EArth atmoe:ph~1--er,• in thP. prenenoo ·of' added Jt2s, have been stua:tbd by l:eyns, \oJalter and Meyer4. These authors paosed a ~k througl) the mixture and they found 'cnr.entially no ettect ot the H~ on the s:mtheses of imdno ac1dr; {non-S containing). They tontat1vcly .ident1.fi0d or.o 3-contn1n1n;~ product. amnoniwn thiocyanate. However, a 5carch for ~-containing amino acids (?Y the Stein'ana ~bore methOdS) ~;·as unsuccessful, although tho authors did rep<?l't ·the preaenee on the1J:' . . Cht'Or.it"l.tO~ramr; Of SiX n1nhydr1n-pos1t1ve, but un1dont1f1ed6 product&. ·~hesc ?.mine nc:tdn may have been aulphur-containilig;. but t~tr yield. wa3 teo t:r.'l<"lll to pcrmU 1dentlfieat1on. .· .. I . ·. .i .' . .. ' ,>( 1 .. ,/. .· ' \ _;·.' "! ·• : .. : / . ' . _,:' ·I . ' 1;" •:··..-.• •• ·' i ··~· .... ' ;,.r. <~· ' .. <··.{ ... ',J ... •.. ~ ,· . . _, .... . " . ' . " . ..: . . ~ . ,., ', - ..... • i 'J'~/.· \o I '~ It sccr.~d to uo to be \'10l'thwli1le to aoarch tor the "pr1mittve-l~h" · .. > I } 4 • . ~ . . ,· r" . ~ .. '" •. . ... •". . .. • . r • )'! reacta."'lto. thun ~;roatly 1ncrcar-ir~ the dotect1on nensitivity tor' an ur.i1no ac1.d product. In thin wt!Y \fC have been able ~ establish the appearance· of cyBte1c acid. aJ3~:cH2CE(NH2 )co2H, and thG clooel)·- · relat~ compound& taur1~, Ho3.(·cn2cHtm2• and cyatar31M• (XH~H~H2 )2 • Cyntcine and cyntine probably v:c-re formed (thero \rnlS evidence for th~ · ln cur early chromatof;rnms) •. but they appea.r.d to be oxidized to cysteic acid durjrJ.IT. suhso/.juant Chron".atography. We found no evidence 'tor methionine pl'·oduction. In eo.ch of the th11.~e exper1.mentr; reported horo; 20 ml of 2 [ tnr,10H, 200 ::m of CE11 • and 100 mn of H235s {oontaininp; 5 me) were placed '1n a \I P?l~x tube ar1d 1rrnd1atcd, \'lith on t"leotron be-run, 1n the trenner pre-viou!lly <1e~cr1bed6. No a.tr h"a/J pror.ent during the 1n"lld1at1.ons. The e1r.ctro."1 cca.-n was uncd for no reason otr~r than that it was a conven1ont ·. \ nource of ton1z1ne; rad:int!on. 'i'he rad1at1on d()~ ~n each case was about 109 rnd3. 7h1s 1s a very high dosej ho'rrevor, our productne as they were formed, were removed rrom tro el~ctron beam (in the condensate dr1rp1ng off a condenr:.er-sae ref. 6) and thus protected from l"ad1at1on decompo-. rs:i.tion. 'l'he 109 r&.6.s Were del1wrecl auring ij5~~e expoSures to the electron bca.":l. After the addition of chromatographic quantities ot unlabeled car-riers (cyntinc, taurine, etc.), the non-volatile cmtents and washinsa from the irradiation chamber ware trnnofel"'red to a round-bottom tl.ask and evaporated to n mrAll volume at room tempera~ure. C@fltrifugation tres then cr:-;rlo:tcd to remove oorne polymrJc matar.Ull. (in:pm-t, elemrmtary ' nul;>t:ur). An aliquot portioo (u~ually O.l) ot t~ concentrated solution 'rtt1s then placed on \•lhatman No. 1 Chrotr.a.togmphio papor •. The solvent 111 ·, . ~; . ·~ . ~ •• ··'•· • 1. ••• ·."', : 1 •.,.' ' ~~ I ! ~·.. : ' 1· I ... . ' I } ·' ~~~ , I ,I. s o I ' ,/ . -. ' _ ~ .r * .~···· .. . / .. .,. t ~ ,; ._.: ,~'.l.f ~ . t.., l ( ( . . ··~ ·; ~ ; .... . .. .. " .... ~·· ·' - ... . ·'f • I '• (.t . . ... • ·:·. l,,. ,, . . . . . • l \ ~ ' .. . ,.',." ~·.-.... : ~., ·~.<~ ~ ... l • • . ·" I! . ,, -3-the first direction~.~~ n-hutru:ol:Acetic ncidt ~ater (l00t22t50, v/v/v){ and, in tr.e second, 1r:.Opropo.r1ol :mcthanoln·:ater (71lt21 v/v/v). PoSitions and sr.,apcs of radioactive ::;;rot:;: ,,:ere dctennined by autoracUography (Kodak "Hue !:-cns1t1ve" rr«11.cal X-ra~~ film). Radioactive apoto with Rr values r;jr.;i lar to t hone of a<lded, cnrr11':'l~ cot;,pc\.u'rla were cut out • eluted • and I rechromato"!':?"nphcd in the follotdng r.olvent syatemnt.. (l) ooo. butanolt fomlc acid (88-90~) n:atcr (15: 3 :2·. v/v/v); (2) nee. Wtanola terte LuWJ1oln:ater (43:~8.4:8.6, v/v/v). On the aecorx1 chranatograms the pa~:ltjons r.u1d ::;r.npen of.' thl2 radioactiVe opots were compared to those or th~ coloured opots rcvealacl by srray1Yll~ the chranatogram with ni.npydr1n r,olution. The arrount or ra<ltoact1v1t:.f 1n a given spot was detenninoo It ! .. ~1tllcr (1) dire-ctly on tho papt"!r by mane of.a 0-.'t counter or (2) after ' ,.... elution, by 1.1quid scintillat:ton counting •. Th1a;~~1QA.ct1v1ty figure c~ulcl .tl;c-:1 .be compared with the total aulOUnt of ~·ss (as n23Ss) that \·:as orif!_innlly prezent in th!.:! i:r-roo1at1on flask'• .'jn this '...ay, the I' · y1eldn of products from the li2~i could tiC determined (due allo~e I . ?'• .. te:lr.g mt;.de for the half life of ./)S). l .. , .. rn,e foliot-r1ng· 35S-labelcd produotl!l (yield from }J235s given paren-thetically) t<.-ere poait1vely :tdcnti.fle<ll cyate.ic ac1c1 (O.OU) 1 cystamine ( 0. 003% ) _. ond taurine ( 0, Ol% ) ,· \·:0 cxpG:cted to fird • and therefore . . intensively searched for• cy~tc1ne,·cyst1ne• and methionine; hOwever, .1r these amino acids are ~ormed, thoir _Yiolds must be wP.ll below o.o~u. · . As was ment:toncd, cyste-ine and cyntine are probably toli'Ded but then d1:-.aop~<.Jr by oxjdation to cyste1c acid. Other compounds for which we se<u•c11ed. but could find no cv:tdence for oynthes1a,_· V&J'O homocysteine and h.');T.oc:n.:-teic acido. It is pleas1ro5· to record that. at least one or the S..Conta1n1nct :· · 'l ' •\ . . ' •. ~.. ' . ,. ··~ l .)· a \ I' • .. ·' ' , . • I • ~ ' • < .. ~ ;~~ : -~ ... :~:;\ .. ' ', >f ·~· -~ . 4. • •• ·~··: • ~ ' I . I \ ' h . '' . . ' t,; .. I .• t . ' :.· . .. · :}, ;;~ ~ f .... . . . •I' ·.···~·· ' .. '· ... ,, . ' t,.; .- . J • • . • ~ ~ a-~~ino ac1d3 (cynteic acid) is formed under "pr1m1t1ve-r~h conditions." i·,'f: believe that others are nl·r~ formed (for ex~le 1 tho cyste1o acid is probably fonned by attnck or the •OH radical on cysteine). ProlJBbly6 rz.all chan;cr. 1.n tho conditions or the "pr1m1tive~h" expcr.imenta (c.::r:., lor.gcr t:trroa or 1rrad~nt1on at low~ dose rates, proaenoe or catn.lytic nurfuccs) t-.111 lead to the 1dcnt1f1cat1ons or all the b1olor;1 cally 1r-:portant t-oontajning amino acids. T:-;! s \·.ork '~-an aponr..orcd in part by the United States Atomic Energy CominGion. It war, aone duri.ng the tenure (1964-65) ot an International Ato;:'!j_c F-1lerc:' Pontdoctoral Fellowship (A. s. u. c .• )-f'l'esent address a · w:·,rcnce RE.diat1on I.nboratOI"J I..<l~JOrato:ry of Chem1cal r:J.odynam1as Univcrn:i.ty of Califomja r:erl.;clcy i Al-tr>iliD S, U" CBOUOrlJUtY 1riol~\·,1_ tz·,. N. H., and Miller 1 S. L. 1 Prot;ress in the Chem1ntrz of the Xntural Product3~ Vol. XX, 1962• p. ~23. 2mner, s. · L. 1 and Urcy, H. c., i.-.ot~nce, 1lQ.; 2~5 (1959). Preen, Net·J liaven, Conn., 1952. ' ·' l! K,, H.-~ynr, • 5.ste1n, H., \·lnlter, \·1. 1 and [~-eyer, [~,, Naturw11'!senMhaften. !.!!} 11 385 (1957)• a1d ~·'ioo:re, s., .J .• p~ol. ·c~:em., 211, 893;. 9.07 .(19514).; · 6Ponnllr.lpel"'UU':la, C., Lor.man 1 H. 1~., r~ariner1 n, t ru¥1 Calvin, M, 6 Proc, >13tl. /\end. ~ct., u.~., !J.1, 737 (1963). ' ...... · ···' ·' . ~ ! . ~· . . •, . r,. . .. . ~ ' •• ·-t.' \ ., ~ ... _ ' . . I, f ,I • • • ·' .... : .. ~~- ~";:~~ ' •. ;. .~.· .. ' - ,. . ' .·1.. i· •t' '• -\ ·'' '. ..... I 0 _.,._ . ,· ~· ' ... ; I ' • ..- ~ '!,: ' I I • I ·: ).·i , ·. : : -~ ' ' . :ll A] . I 

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PRODUCTION OF CYSTEIC ACID, TAURINE, AND CYSTAMINE UNDER PRIMITIVE EARTH CONDITIONS

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PRODUCTION OF CYSTEIC ACID, TAURINE, AND CYSTAMINE UNDER PRIMITIVE EARTH CONDITIONS

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