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FY 1992 Report on Results of the Research and Development of the Technologies for Creating/Processing Advanced Biomaterials

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FY 1992 Report on Results of the Research and Development of the Technologies for Creating/Processing Advanced Biomaterials (± t J6 t A'y;iziggrffl#coSSffik iSIBiStSfc * OWK-teS: vt. 0#mB*ESE*<7)®tt*H. mU>II4IJ<r>fi±bZtLi3Uh* f LT4% $$E*<7)SiJSiak LTcoiltSL &^«E«S-(bfcff3k«<F> e«(i^sa§»«ffl^sfcv^„ m^&m&ztiizmix. 4ss&- ^E^fc^tOlSliri^EAflJo^SitSr^SL. #t»mm&&<CkU##TU»n. iWS-fkfr B8 -t5Sfc<fc 9 Sbt&*fi£&Sk k *>£. f«SlkL TtStl^L^royi? k£E5gU 3 . -E-LT-e^Silfc<t 0Silfl6#tAV'>riiB*<OA'7yx<O$!#iit%Bk-eiLfcj:<.Tt>yk 6.$ji63E9 ILykti:Sco 5l3®K $41"'E.^k»iS<rcO*S-e&? lk!®k-TV^„ SMBT'tt. gtfcSSISWSSStoESfcJ: 9 rs|g$«fctitt6#|sl8ffim%T--7to%SM$j f(0*S@^fE4#3BC&kA. 34f-vkiSf-vkLtgglt. -E-(0*T st*«fct3tti.M4'*5E^k#i.A.ti.ft«^ rj xh^tz. T- a®SSBIB8«E • SB$t£&mfl%Bfl%rn:/'x:? h k LT r^%A A *1E9 ±if^.fL. SMfflti¥E4^1 2^17B. Sfx*^ - ■ ESteffrE^rS%E«J: *7nyxnil, im<03i£ f—7(03 7° M=#4t«0#E(cJ5 f-eroggcoBEtCtt. A'4*S$$rSk LTE^»><9ll&6mij$«(9«iEHk»s!£ mxhtif. 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BiBBi:* 3 S 2 S : f - H (O-S-ESri gaswb^jfc .........................................................................fflssa i 3 Total Synthesis of Nephritogenic Glycopeptide, Nephritogenoside • • • Sift ZB 22 rnf-r—tffc-tSx^rf-Hwti^Rjefc-ovvc • • • a e®. »*ss 2 e S3S: a / F/\<om 9 a* Stereoselective Routes toward the Synthesis of Unusual Amino Acids • • ■ *«&** 3 5 i 7r-f yy^invx^nmm ■ ■ ■ #JH IE, ffl# m 4 2 5 y SE^9 2= A .........................5*FSS 5 1 Chemistry of Lantibiotics ....................................................$ 5 9 S4S : ^7f-F«flS£jj?ifr fab»*»yr<osiEk h ■ • ■ •eUSX, TBSM 8 5 .........................mwmw. 9 0 S5S : < 7" f-F <948 *51$ ##K*5i$&$f FE f <9 @m ........................... ±er* 9 7 meg : nmm t mm%M ..........................................................................±® $$ 109 A low-cost,high-efficiency solar cell based on dye-sensitized colloidal Ti02 films ■ ■ • B.0'Regan & M.Gratzel 12 0 Development of Specific Immunoadsorbent Containing Immobilized Synthetic Peptide of Acetylcholine Receptor for Treatment of Myasthenia Gravis • ■ ■ i 2 3 jiimeil 12 7 I? m : s<J3- KI^©E Lecture 1. (ac&ic Tb^TrS ao "37 0, 7 ; y#&Lb#W4-(synthon)6 LT, me7% &, wb#j (Dfct ixm L%, #A^7; y ^^tr<77 r #^ac, m ©fffli§7bN b ©## t) °J£b o £££!£!+ L LT^ < Ci(t #&©A#c## 2) 7©^# twmgT&ao #C#3<!= Wb#J A^©me(i2o@m©7; y^cj;( 9 %mc$^ao (d:, 7©#r^7##K#(c7L/-7 x 6YiT c ti^ioBSo nc u/cYftj-eio 13 #^©^77b<w#T ua6^AZ3o f:t\ C©Z 3 &ao A6%7 = y@g^m^a(Z$ Lua^#^f##o#&6LT r/<y^r%#j %a aD L'7b'<c#7IxSf tcii LtzftX-Xha/bvb71P$ ti aD Etc, AS©M6S£E©iWEE • ^ 3) <77 K0^CU3#^MA#^fcj;D#$c$;h,a c^zb), ^7^#t, H?m- gui^o l^u uw±£(D£mfr)U ^#r&ao g (hti-oTVSo a c a 7b^emo#im^#-© /<77FZ#(d:CO^>8%%#^^^mLT, Zb) 7&fcZ *)&j£L&&RJimti<Mfrtifi:0 wm^mt 7©#m ^mz c © z 3 a—fi£t£©£> a ema&wgaam&m^T, , ##&#$# ;l/- <, ^-o@7b^ fcegff $naMcb v^xZ 3 o 7th'j>/77^ -&m i ^ts—©$s±tc7s m#^^ao ^<77K^ML, 7©##^#^^^^C##f f >amz#6/<77 K%#o#±omu(m#^ a^WFodor^CZ^Ttg^freua^o * A.^O20fI^I©7 ; 7 EEA£;b-ti:(C|$b:ha©tC*t efi^m^a c 6 cz -3T##T^#%<77 r L, ##7ti#A#7 ; y#&5Wd#7 ; /ESynth ©7^ 77 V — ©S^Tb^DjtbT^)ao "7 r — v©ill {7 on$<-Xi LT£#:£/&^©#£C^./•cfiJffl^S?^' f (:7 >yA(:^^$-dr/cigmE^J^Ea'i6/LT B#6LTdo^, 6'L6m#%^fn:#:0)-##6LT 10'-'©#^^/:##©<77 K^#ac6^=im6 {^.H-d ty ^tia^tc® §o ^-oTua"') <77 K^47%#m(c#m LZ 3 67 ama-(d:% 4) <77 KIeJSoEd, i>at'(i2 3©Y7f F7© mm##7b<jt##s# c a« i\ L^L, <77 KEA^<-xc7a6^3A7(d: <77 K^fM7a7 ; K#A(i, %S • 6#/Zb)^'^A^##T&ao %-oT. ^<77 K i^< c6A<^-e&o. emm%m%m#:©±&©± (m6%m©m%7b^#-c&ac67b^, (:, L-3 7b^6L/:^A^^^^<C67b<^#$ti ##6 LT^#fac6tpi#-e&ao 6o 5) $-#5% L#Uo <77 K(t 5>7rB17(cZ 0 g 2. <7°7 K%^©## COZ3^#m^#m^(Z—3©/<77 H7}7(cf 1) 7 ^ V lIC V 3 ^1$t40r^Vsynthon^^JffiT -S ^T©##^#$4ta©-e(i^<, u<-oW)#7 6o LT#r/:^#m^^m$-dra C 7 ; y E£-/&ic§H LTl2EtcM7b<B3:lT£> D, 6^#<k^ao COZ3^#x.^(j:, AZ^-;l/#4; m ^ L i 7; y me7^^#tf a c 6 c z 7©iii t)#x.a £>©t£> a0 b), <77H7>74:(cm^^##&©#A^^ac6 6) ^%#^$j#7b<jt^mg#T&ao -1 - #L'/:6C6T^6o t Lrfijffl ltv< ±X'<D^mmi<Dm\L*mz> ztw it'MtmmcD’^.m^mm^mmt6±Ti-itm^xm 4. /<Y^ KX^tDESEtfi -Bo CtlbtilA$5^spatial arrangement^-"5J#6 LTti 1) ##T# 6 J: 9 C^:-3i#ef KA 2) m#7; y ^c(D^9 —o(D^:#^:V-;l/T^6o C(Dj:9/C#% 3) 4) K(DAR%%# ^tltl^o Tirrell f£ C © «fc 9 LU s) MftTttffc'&fct? L/c5ff^;£r:ii|ia6Tl''-B6) oCappello 6) Ii7-f7"a * ? 7 T) 7 K£)?££tf ^Tl'^’o CCDJ:7(C, ^fi©t#oj£ 8 ) nc«t-3T#mL«t9 6f &:&&# 9) K(:^(d6%f89## 10) ©EE^‘±(f ^ tiB>o Mi" L LII3S L/c L©TWj:v 3. K©fUffl#& /)\ 4#c(D^^m]ZLiru<±T^RT^^L(D(^ #l\ B*T(d: B, c «h c «h W<hLT#mcLTU< C6 4)W#T*6o t)'fc> -Bo (/w^v-7-t;K @mm7cWK [#%:&#] 2) ^####6 LT®4# 1) S.P.A.Fodor,J.Leighton Tead,M.C.Pirrung,L. LT*) «P. Stryer , A. T. Lu, D. Solas, Science ,251, 767 (1991) 6 C 6 2) S.E.Cwirla,E.A.Peters,R.W.Barrett,and W.J. B>C6*<^T&6o $/:##^(Dm^/j:spaciala Dower,Proc.Natl.Acad.Sci.,87, 6378 (1990) rrangementC ct K> < ©Tfe^^MttT^WMX' c? =L 7 3) J.J.Devlin,L.C.Panganiban,P.E.Devlin,Scien- ce,249, 404 (1990) 3) ma#m#46LT(DWB 4) J.K.Scott and G.P.Smith,Science,249, 386 (1990) ##%#&&86 5) J.Cappello and J.W.Crissman,Polym.Prepr.,30 {cSJ®LT^-BCch^"5JtET*-Bo (1), (1990) 6) K.P.McGrath,D.A.Tirrell,Polym .Prepr.,31(1), 4) LT<zmm 190 (1990) /<y^ KcD^-o^f LT&@#?o lr^y*r-t LT^fiJffl^-e^>B)o m&3#m r/<7f , p i - 3, 5) ^##$46 LTOfUffl D) <-??- Kte£&3£.iz&HktB>W*4T £> B> C <h G > A#®# ^&##%L/c 6 C 6A<-e# B,o (#%mAM#4s mm###$4) K&<-x6f &#?%#(;#:# tint LrtiiWEr* b,c t. &m<imvjr)§ci^ zomm&ffi - 2 - C0>I *2 ’ EE tl: ** Quantitative Analysis and Prediction of Hydrophobicity of Oligopeptides Miki Akamatsu* and Toshio Fujita* The log P value used for the hydrophobicity parameter, where P is the partition coefficient in a 1-octanol/pH 7.0 buffer system , of a number of di—pentapeptides was analyzed with physicochemical parameters for the side chain substituent of component amino acids. The log P value was shown to be governed not only by the “intrinsic” hydrophobicity but also by the steric effect of side chain substituents as well as intramolecular-type solvation and “polar proximity ” effects for polar side chains. The yff-turn conformational parameters of compo­ nent amino acids devised from the Chou-Fasman propensity index were nicely applied for the analysis of log P value of tetra- and pentapeptides. Using the results of the correlation analyses for logP of oligopeptides, we proposed a new effective hydrophobicity scale. na, for unionizable amino acid side chains. This scale and the hydrophobicity of oligopeptides would be useful not only for the process of peptide synthesis but also for the quantitative analysis of the structure-activity relationship of bioactive peptides. Key words : Oligopeptides ; Hydrophobicity : Partition coefficient; Peptide synthesis ; Drug design. # s ti-c v &4-5,0 1. -M-th ROD K3,£ V z-tzzt nTfg & 6 If, WrLi'ES, ammaUBWKa tU> X n i: £ O X £ tzo iis 20-30 6 ^ 6 v yf- L, 6 Ztlt2 -cw&o S .1 <!: liw ^ 5T&&V', 5Z:£2(7)S;S§li, K(7)^St5-14o5S $ t till *) si-mr-***?■? u t T-'¥<DMfr t-M2mi:RimLTw6, -&u, #m(7)Emm^imm * (t606 c t icfca-e * Faculty of Agriculture. Kyoto University (Kitashira- kawa Oiwake-cho, Sakyo-ku, Kyoto 606, Japan) Hansch &«'. — 3 — ( 41 ) y v y^yy 837 Free-Wilson j£9 >£(Z £ tlfijffl 7r=log px—log P„ (1) s/vcs/jo ^yy m^<7>E5yyft£-timz, z<dx * izz&sx t, > utz&&, mmitb L^;i%n^ L/zB# • #60 2(7)Z9<C#^, logP (Z###% S«LTSTV^0 gH^LX, ifii5EKT£te£7jvf*y #^(7)logP ^ (7)#^#^ Lxmt>ztiz>0 yv >####:MY-5561"), ^#^j(7)yMyy K">£t* fip*> 6nfiK1±y»?fiK3l-y &<r>X, —&lZ%:j®it&y}<D logP lZ(5t 2)H Z o xy#W#X^a% log P=log Ph+E^-x ( 2 ) @#xy#&%#jem/zy/z#% /<yy Ld'L, x /: 0, # itrS&m;££g<B#niz, ^yy Ko^y^zaziy me:e g 1 # 2 y#^n iz, Kw.&t l m eemy^cL L^aamt)Ziao ymv\^K6##t(o^m%i:^LTBwe4-y6o m &±<Dztfrb, ^yy kzs,1:vrz<Dm&fc<Dm*& y > -tf > <o#^n iz, t:% tm&tcom&tmtfl, #Fmy6mwj^#< c^i± =fM&X Tf±Lfcm^*Jktf1rtztb, logP @Axmm:y#v^ z/z/<yy Kmawctze, #&7 5 y 21 iz, V'21)0 7 ^ >2y, t^yTy^ ’^^AroTO y ^yy Kszc/y >/< %(7)#^t^#"e^6o %cT, -fei:iM^O y w t &&b t (Dtezimvmw c^u-ct log P (i, log P„ i: Z^S X <7)“y^O ”i^7K14io Z Cff x-hho LfrLftnk, ^yy K^yg#^7Ki4^ov^ tLtiL^|-(7)^fc<7)fatJZo'C(^:3)(7)Z 9 tJE^^tL^) ^tuzsyib < :i:iy^ 2,-2,o ^yy K^2#m±<7)##me# Lx^-my >#ax log P=aE^x+Eb|E,+log P„ ( 3 ) Ml, E, ti, Hx & &?&&*• ¥-?%&;< y - y <Dfcm*mmx$> ^tzfrb 7*-?x, v^rn<> h tmmztZo a, Miytiy Xhhlo C(7)Z9^^#C*cX, 6S, 3%4(jx<> y^yy K$T*(7)jt^gss<7)^yy roi&7Kt4</>*iS Xhh logP„ LX^fahti, tiiil-Yfrtt: 1- y y y y - P log &fXb&4w$mlog? lx, sy-^ p &, y^#%T < y cm-y < m@#^cz ^x^y>^ti^> 0 n m&#< z.ttfx£fzn-u)<Dx, ycommc^^ycc a l± 1 (J#L< %2>lti*X&2>o C(7)Z 9 tJ LXSt5'/l /j^r^^^ibv y&fk^oiogp tym-yactmT BfcL^a0 2.
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