UNIVERSnATSrilbuu. •"' '

HANNOVER i

TECHNfSCHE

WFORMATIONSBIBUOTK .

SYNTHETIC OLIGONUCLEOTiDKT"PROBLEMS AND FRONTIERS OF

PRACTICAL APPLICATION''°"

v

SHEMYAKIN INSTITUTE OF BIOORGANIC CHEMISTRY

USSR ACADEMY OF SCIENCES

MOSCOW

JUNE 23-30, 1991

Organizing Committee:

D.G.Knorre, V.A.Efimov and O.G.Chakhmakhcheva

UB/TIB Hannover 89110 455 258 I

NUCLEIC ACIDSSYMPOSIUM SERIES

No.24

OIRLPRESSat

OXFORD UNIVERSITY PRESS

Contents Nucleic Acids Symposium Series No. 24 1991

Forewordxv

The synthesis and antiviral activity of some 4'-thio-2'-deoxynucleoside 1

analogues

M.R.Dyson, P.L.Coe and R.T.Walker

Progress toward the synthesis of nonionic oligonucleotide analogues with 5

sulfonate and sulfonamide internucleotide linkagesJ.A.Secrist III, P.A.Crooks, J.A.Maddry, R.C.Reynolds, A.S.Rathore,M.Shamim Ahktar and J.A.Montgomery

Synthesis of branched nona- and deca-RNA modelling the lariat formed 9

in pre-mRNA processing reaction (splicing)C.Sund, A.Foldesi, S.-I.Yamakage and J.Chattopadhyaya

Investigation of DNA biosynthesis catalyzed by DNA polymerases: 13

approach of synthesis of compounds with anti-HIV activityA.A.Krayevsky, N.B.Tarussova, M.K.Kuhanova,J.Balzarini, E.DeClercq, E.V.Karamov and V.V.Lukashov

Hexopyranosylnucleoside 6-triphosphates are not substrates for DNA 17

polymerasesS.N.Mikhailov, E.V.Efimtseva, N.Sh.Padyukova, Z.G.Chidgeavadze and

R.Sh.Beabealashvilli

Diadenosine oligophosphates: peculiarities of synthesis by phenylalanyl- 19

tRNA synthetases from E.coli MRE-600 and Thermits thermophilus HB8

A.I.Biryukov, V.N.Ankilova and O.I.Lavrik

Bifunctional properties of analogues of modified nucleotides: immune 21

system cells stimulation and human immunodeficiency virus (HIV)

replication inhibition

V.M.Pisarev, N.B.Tarussova, V.P.Leskov, S.G.Kremlev, M.K.Kuhanova,

A.V.Tutelyan, E.D.Otrazheva and L.A.Pevnitzky

Acyclic analogs of dideoxydidehydronucleosides 23

A.V.Tsytovich, M.V.Kochetkova, D.V.Philippov, B.I.Mitsner and

V.I.Shvets

Studies in the synthesis of oligo- and poly-ribonucleotides 25

C.B.Reese

New approaches towards automated oligoribonucleotide synthesis 29

W.Pfleiderer, K.-P.Stengele, M.Mohr and F.Bergmann

Solid phase synthesis of mRNA by the phosphoramidite approach using 33

2'-0-l-(2-chloroethoxy)ethyl protection and its stability in E.coli system

O.Sakatsume, T.Yamaguchi and H.Takaku

Contents continued overleaf l

Further improvement in protecting method for the oligonucleotide 37

synthesis in terms of a cellulose acetate derivative as a polymer

support

K.Kamaike, T.Ogawa, Y.Inoue and Y.Ishido

Large scale automated synthesis of oligonucleotides 41

A.Andrus, H.Vu, P.Ramstad and M.Pallas

Synthesis of some oligodeoxynucleotides containing the C-nucleoside and 43

2'-deoxy-2'-fluoronucleoside moieties

I.Rosenberg, Z.To£ik and K.A.Watanabe

Synthesis of oligoribonucleotides by the H-phosphonate approach using 47

base labile 2'-0-protective groups

E.Rozners, V.Kumpins and E.Bizdena

Rapid deprotection procedures for synthetic oligonucleotides 49

N.N.Polushin, I.N.Pashkova and V.A.Efimov

Structure—function relationship of hammerhead ribozymes as probed by 51

2'-modifications

W.A.Pieken, D.B.Olsen, H.Aurup, D.M.Williams, O.Heidenreich,

F.Benseler and F.Eckstein

Synthesis of site-specifically modified oligoribonucleotides for studies 55

of the recognition of TAR RNA by HIV-1 tat protein and studies of

hammerhead ribozymes

G.Slim, C.Pritchard, E.Biala, U.Asseline and M.J.Gait

2'-0-Alkyloligoribonucleotides, synthesis and applications in molecular 59

biology

B.S.Sproat, A.I.Lamond, R.G.Garcia, B.Beijer, U.Pieles, M.Douglas,K.Bohmann, M.Carmo-Fonseco, S.Weston and S.O'Loughlin

Separation of [Sp]-3'-0-(5'-dimethoxytritylthymidyl)-S-0-(3'camphanoyl 63

thymidyl)-0-methyl phosphiteA.Wilk, B.Uznanski and WJ.Stec

Specificities of rabbit anti-(2',5')oIigoadenylate antibodies towards 67

phosphorothioate and seco analogs of oligoadenylatesI.A.Mikhailopulo, E.I.Kvasyuk, T.I.Kulak, S.M.Shulyakovskaya,M.V.Makarenko, S.N.Mikhailov, R.Charubala and W.Pfleiderer

Studies directed towards efficient synthesis of oligo-5'-deoxy-5-C- 71

(phosphonomethyl)deoxyribonucleosidesJ.Stawinski and T.Szab6

The 2-(acetoxymethyl)benzoyl group: a new base-protecting group, 73

designed for the preparation of labile, modified oligonucleotides

W.H.A.Kuijpers, J.Huskens and C.A.A.van Boeckel

ii

Synthesis and properties of modified oligonucleotides 75

R.L.Letsinger, R.A.Alul, F.Farooqui, S.M.Gryaznov and O.Kinstler

New synthetic approach to nucleoside phosphorofluoridates and fluoridites. 79

Novel type of phosphitylating reagents containing 4-nitrophenoxy group

J.Michalski

Backbone modified oligodeoxynucleotides: stereoselective synthesis of 83

methylphosphonates and HIV inhibitory capacity of phosphorothioates

J.W.Engels, T.Daum, A.Frauendorf, S.Liiking, M.Mag,

W.E.G.Miiller, J.Muth and P.Rosmanitz

Solid-phase synthesis of oligo(2'-deoxyxylonucleotides) and PCR 87

amplification of base-modified DNA fragmentsF.Seela, H.Rosemeyer, M.Krecmerova and A.Roling

Synthesis and biological studies with dithioate DNA 91

M.H.Caruthers, G.Beaton, L.Cummins, D.Graff, M.Hall, W.S.Marshall,

H.Sasmor, and W.Wiesler

Synthesis and some reactions of nucleoside H-phosphonothioate esters 95

J.Stawinski, R.Stromberg, T.Szabo, M.Thelin, E.Westman and R.Zain

Design and applications of single and double stranded DNA analogs 99

Z.A.Shabarova

A new approach to stabilize complementary complexes formed by short 103

oligonucleotides and their derivatives

V.F.Zarytova

Effect of magnesium ions and low pH on interaction of pyrimidine 107

oligonucleotides with dsDNA: affinity modification study

E.Brossalina, E.Demchenko and V.Vlassov

Structural and kinetic problems of sequence-specific modification of 113

nucleic acids by reactive derivatives of oligonucleotides

F.Olga and P.Larisa

2D NMR and molecular mechanics structural studies on the 115

oligo-nucleotide duplex d[p(TGTTTGGC) ].d[p(CCAAACA) ] and

its modified derivatives

E.V.Bichenkova, T.V.Abramova, Yu.N.Vorob'ev, V.F.Zarytova,

E.M.Ivanova, T.V.Maltseva and A.V.Lebedev

Comparison of anti-RNA properties of normal and ellipticine 117

functionalized a. and /3- oligonucleotides

M.Lavignon, J.R.Bertrand, H.Porumb, B.Rayner, J.L.Imbach,

C.Paoletti and C.Malvy

Inhibition of reverse transcription by unmodified and modified antisense 121

oligodeoxynucleotidesC.Boiziau, C.Blonski, N.T.Thuong, D.Shire and J.-J.Toulme"

Contents continued overleaf iii

Oligodeoxynucleotide hybridization inhibition of HIV and influenza virus 127

P.C.Zamecnik and S.Agrawal

Design of bifunctional oligonucleotide intercalator conjugates as inhibitors 133

of gene expressionC.Helene and N.T.Thuong

Oligodeoxynucleotide analogs as informational drugs to regulate 139

translation

M.Ghosh, K.Ghosh and J.S.Cohen

Complementary directed modifications of nucleic acids and oncogene- 143

directed mutagenesis in vivo

N.Grineva, N.Satz, V.Pantin, G.Solovjev,

V.Surin, A.Krutov, T.Borovikova and E.Shukova

Nuclear location of synthetic oligonucleotides microinjected somatic cells: 147

its implication in an antisense strategy

N.Mechti, J.-P.Leonetti, J.-P.Clarenc, G.Degolsand B.Lebleu

Antisense oligodeoxynucleoside methylphosphonate inhibition of mouse 151

c-myc p65 protein expression in E^c-myc transgenic mice

E.Wickstrom, T.A.Bacon, E.L.Wickstrom,

C.M.Werking, R.D.Palmiter, R.L.Brinster and E.P.Sandgren

Mode of uptake of 5'-cholesteryl-linked phosphodiester oligodeoxy- 155

nucleotidesin HL60 cells

C.A.Stein, L.Yakubov, L.-M.Zhang and J.Tonkinson

Utilization of antisense oligonucleotides in vivo: stability and 157

internalization of hydrophobized oligonucleotidesS.de Falco, A.Boutorine, Cde Smidt, T.van Berkel, E.Saison, C.Helene

and T.Le Doan

Stabilization of PyPuPu triplexes with bivalent cations 159

M.D.Frank-Kamenetskii, V.A.Malkov, O.L.Voloshin and V.N.Soyfer

Synthetic gene design to investigate the role of cw-acting DNA structural 163

elements in regulation of gene expression in vivo

S.K.Brahmachari, P.S.Sarkar, P.Balagurumoorthy, P.K.Burma

and R.Bagga

Parallel double stranded helices and the tertiary structure of nucleic acids 167

V.L.Florentiev, O.F.Borisova, B.P.Gottikh, I.A.Il'icheva, Yu.P.Lysov,

O.K.Mamayeva, B.K.Chernov, A.A.Chernyi and A.K.Shchyolkina

Parallel stranded DNA under scanning tunnelling microscope: the main 169

characteristics of the double helix

N.A.Tchurikov, Z.Jing-de, Li.Min-quan and B.K.Chernov

tv

Modification of duplex poly(G)-poly(C) by platinum (II) compounds 171

G.A.Platonova, E.M.Kogan and N.S.Sidorova

Scanning of key residues in antibody binding sites by two saturation- 173

mutagenesis approaches

S.A.Narang, D.A.Brummell, V.Sharma, D.Bilous, G.Dubuc,C.R.MacKenzie, J.Michniewicz, J.Sadowska, N.Anand, N.M.Youngand D.R.Bundle

Atomic structure of a pyrimidine-dimer specific excision-repair enzyme 181

from bacteriophage T4

K.Morikawa, O.Matsumoto, M.Tsujimoto, K.Katayanagi, T.Doi,

M.Ariyoshi, M.Ikehara, T.Inaoka and E.Ohtsuka

Oligonucleotides and their derivatives as tools for investigations of 185

protein—nucleic acid interactions in template biocatalysisO.I.Lavrik

Hybridization properties of gel-immobilized oligonucleotides 189

I.B.Ivanov, K.R.Khrapko, B.K.Chernov, A.A.Khorlin, Yu.P.Lysov,V.L.Florentiev and A.D.Mirzabekov

An oligonucleotide matrix hybridization approach to DNA sequencing 191

A.A.Khorlin, K.R.Khrapko, I.B.Ivanov, Yu.P.Lysov, G.K.Yershov,

S.K.Vasilenko, V.L.Florentiev and A.D.Mirzabekov

Synthetic oligonucleotides for biomedical applications 193

H.Seliger, A.Frohlich, G.Groger, B.Krist, M.Montenarh, H.Rosch, R.Rosch

and F.Ramalho Ortigao

Branched DNA amplification multimers for the sensitive, direct 197

detection of human hepatitis viruses

M.S.Urdea, T.Horn, T.J.Fultz, M.Anderson, J.A.Running, S.Hamren,

D.Ahle and C.Chang

Branched oligodeoxyribonucleotides for use as amplification multimers in 201

bioassays: chemical synthesis and characterization

T.Horn, C.-A.Chang, T.J.Fultz, D.Ahle, S.J.Hamren and M.S.Urdea

Synthesis and properties of branched and hyperbranched oligonucleotides 203

M.J.Damha, R.H.E.Hudson, K.Ganeshan, S.V.Zabarylo and Y.Guo

Non-radioactive labelling of oligonucleotides with pre-functionalized 205

phosphoramidites or H-phosphonates during automated synthesis

D.Cech, F.Schubert and U.Moller

An approach to the synthesis of multilabeled oligodeoxyribonucleotide 207

probes

S.Gryaznov, L.Loginova, V.Potapov, D.Stecenko and S.Veselovskaja

Contents continued overleaf v

The structure and application of oligodeoxyribonucleotides containing 209

modified, degenerate bases

D.M.Brown and P.Kong Thoo Lin

Mutagenic properties of oligonucleotides with modified sugar-phosphate 213

backbone

V.A.Petrenko, G.A.Kuzmicheva, S.I.Tatkov, L.I.Karpenko and A.A.Ilyichev

Synthesis and modification of genes through artificial splicing by 215

directed ligation (ASDL)

E.N.Lebedenko, K.R.Birikh, O.V.Plutalov and Yu.A.Berlin

Study of the mechanism of EcoRII endonuclease activation with synthetic 217

substrates

E.S.Gromova, O.V.Petrauskene and E.A.Kubareva

The use of synthetic oligonucleotide primers for amplification of a 219

variable number of tandem repeats loci for paternity testingV.V.Nosikov, I.V.Ovchinnikov, D.K.Gavrilov and M.V.Chelnokova

Use of synthetic oligonucleotide probes for investigation of tick-borne 220

encephalitis virus genetic variabilityV.I.Zlobin, V.A.Shamanin, D.A.Drokin and A.G.Pletnev

Applications of oligonucleotides bearing single and multiple labels 221

introduced during synthesis

S.J.Fowler, I.Durrant, M.J.Gait, K.Misiura and M.R.Evans

Use of the amidite chemistry in the PEG-supported, large-scale synthesis 222

of oligonucleotides. The 'HELP Plus' method

G.M.Bonora, G.Biancotto and C.L.Scremin

Characterization of synthetic branched DNA (BDNA) using 223

polyacrylamide gel-filled capillary electrophoresisC.Chang, D.Ahle, M.S.Urdea, D.N.Heiger and B.L.Karger

Synthesis of oligonucleotides modified in the sugar moiety 224

K.Augustyns, F.Vandendriessche, A.Van Aerschot and P.Herdewijn

Synthetic oligonucleotides as models of superstructural features of 225

regulative DNA sequences

S.Cacchione, F.Bordin, M.Savino and A.Tufillaro

Theoretical prediction of sequence dependent DNA superstructure and 226

their gel electrophoresis behavior

S.Cacchione, P.De Santis, D.Foti, L.Leoni, A.Palleschi, G.Risuleo

and M.Savino

Synthesis of diribonucleoside thiophosphates via stereospecific 227

sulphurization of H-phosphonatesH.Aimer, J.Stawinski, R.Stromberg and M.Thelin

vi

Studies on reaction conditions for ribonucleotide synthesis via the 228

H-phosphonate approachJ.Stawinski, R.Stromberg and E.Westman

Convenient synthesis of dinucleotide methylphosphonates 229

J.Stawinski, R.Stromberg and T.Szabo

Some chemical and stereochemical aspects of oxidation of nucleoside 230

H-phosphonothioate diesters

J.Stawinski, R.Stromberg and R.Zain

A convenient procedure for the synthesis of S'-dimethoxytrityl-2'- 231

deoxynuc!eoside-3'-succinates and for their attachment to solid supports

Yu.L.Hripin

Incorporation of point modifications into oligonucleotides during 232

automatic synthesis

E.A.Romanova, E.M.Volkov, L.G.Kuznetsova, T.S.Oretskaya and

Z.A.Shabarova

A convenient approach to the synthesis of nucleic acid bases allenic 233

derivatives, possessing anti-HIV activity

M.V.Kochetkova, A.V.Tsytovich and B.I.Mitsner

Super-rapid synthesis of oligodeoxynucleotides on a micro-scale 234

V.P.Kumarev, V.F.Kobzev, K.D.Kuznedelov and Yu.G.Sredin

Design of new DNA duplexes containing chemically cleavable 235

internucleotide bonds

S.A.Kuznetsova, M.G.Ivanovskaya and Z.A.Shabarova

An efficient synthesis of 3'-mercaptoalkylated oligodeoxyribonucleotides 236

on the universal solid support

A.P.Guzaev

Simple solid phase synthesis of amino-oligonucleotides for obtaining 237

non-radioactive probesV.P.Veiko, K.I.Ratmanova and A.S.Osipov

Nucleoside 5'-(a-methylphosphonyl)-(8,7-diphosphates as substrates for 238

DNA polymerases

N.B.Dyatkina, L.S.Victorova, A.M.Atrazhev, D.Ju.Mozzherin

and M.K.Kukhanova

The synthetic oligonucleotides as a model for studying of DNA folding 239

M.Z.Gorgoshidze, E.E.Minyat and V.I.Ivanov

Modification of polydeoxynucleotides by a 'switched on' oligonucleotide 240

reagent activated in different ways

S.I.Oshevski

Contents continued overleaf vn

Structure and biological activity correlation for some nucleoside 241

analogues—inhibitors of reproduction of human immunodeficiency

virus (HIV-1)

G.V.Gurskaya, A.V.Bochkarev, E.N.Tsapkina, A.S.Zdanov

and A.A.Krayevsky

Optimization of the program for automated DNA synthesizer, model 242

380B (Applied Biosystems)

N.S.Bystrov, O.M.MoIokoedova and I.V.Severtsova

Solid phase synthesis of oligoribonucleotides 243

V.Kumpins and E.Stankevich

Oligonucleotides modified with phenazine derivatives 244

V.L.Makitruk, S.N.Yarmoluk, A.S.Shalamay and I.V.Alexeeva

Sequence specific chemical modification of single- and double-stranded 245

DNA fragments with reactive oligonucleotide derivatives

S.V.Mamaev, T.M.Ivanova, A.A.Koshkin, O.V.Semuchina, T.S.Godovikova,

D.S.Sergeev, V.F.Zarytova and V.V.Vlassov

Sequence-specific modification of nucleic acids by oligonucleotide 246

derivatives with an alkylating group at C-5 of deoxyurldine

A.S.Levina, L.M.Khalimskaya and V.F.Zarytova

Effective sequence-specific photomodification of nucleic acids by 247

oligonucleotide derivatives bearing aromatic azido groups

D.R.Tabatadze, M.I.Dobrikov, A.S.Levina, T.A.Prikhodko, G.V.Shishkin

and V.F.Zarytova

Sequence-specific photomodification of DNA by different porphyrin- 248

oligonucleotide conjugatesK.G.Shoikhet, A.V.Kazantsev and O.S.Fedorova

'Quasi-enzyme' cleavage of a DNA target by a bleomycin A5 249

oligo-nucleotide derivative

V.P.Zarytova, D.S.Sergeyev and T.S.Godovikova

Estrone and 5-X-dihydrotestosterone oligonucleotide derivatives 250

E.M.Ivanova, V.F.Zarytova and LA.Pyschnaja

Biological and physico-chemical study of ara-AMP conjugates 251

F.P.Colonna, L.Fiume and V.Viti

Direct selection vectors, promoter-active adaptors and their use for gene 252

assembly by a single-stranded cloning method

M.-L.Tjornhammar and A.Simoncsits

Cocrystallization of Escherichia coli RNase H with synthetic DNA/RNA 253

hybrid oligomersM.Ishikawa, Y.Oda, K.Katayanagi, S.Iwai, E.Ohtsuka and K.Morikawa

via

An efficient method for localized mutagenesis 254

S.I.Tatkov, O.Yu.Smirnova, B.A.Illarionov, A.A.Ilyichev and V.A.Petrenko

Investigation of structure-function relationships in procaryotic promoter 255

using synthetic models

O.N.Koroleva, V.L.Drutsa, A.V.Krivonos, V.N.Sergeev and A.V.Terskich

Estimation of the in vivo mutagenicity of artificial inserts in DNA 256

V.L.Drutsa and P.Bednarek

The uses of synthetic oligonucleotide primers for prenatal diagnosis of 257

sex in chorionic villi via the polymerase chain reaction

D.K.Gavrilov, I.V.Ovchinnikov, M.V.Chelnokova and V.V.Nosikov

The use of PCR technique and sequence specific oligonucleotides for 258

HLA-DQA1 and DQB1 gene typing in a group of insulin-dependent

diabetes mellitus patients in the Russian population of Moscow

D.K.Gavrilov, I.V.Ovchinnikov and V.V.Nosikov

Using oligonucleotide primers for intron excision from human genomic 259

interleukin IB gene by means of PCR technique

D.A.Christyakov and V.V.Nosikov

Oligonucleotide derivatives resistant to the cell nuclease degradation and 260

effective for the RNA hydrolysis by RNase H

M.B.Gottikh, N.F.Krynetskaya and Z.A.Shabarova

New technology non-enzymatic assembly of a gene 261

I.N.Merenkova, N.I.Sokolova and Z.A.Shabarova

Sequence specific alkylation of dsDNA by 2-chloroethylamine derivatives 262

of purine oligonucleotidesE.Brossalina, E.Demchenko and V.Vlassov

Preparative solid phase synthesis of a tetradecamer r(GAUUGAAAAU- 263

CCCC) by the H-phosphonate method using a 2-0-tetrahydropyranyl

protective group

A.G.Venyaminova, M.N.Repkova and T.V.Maltseva

Synthesis of oligo(2'-0-methylribonucleotide) derivatives carrying 264

5'-hydrophobic groups and thermal stability of their duplexes

A.G.Venyaminova, Z.A.Sergeyeva, S.G.Lokhov and M.N.Repkova

A new method for introduction of steroid residues in mono- and 265

oligonucleotides via H-phosphonates of hydroxysterols

A.G.Venyaminova, Z.A.Sergeyeva and V.Z.Bashirova

A new method of synthesis of 3'-mercapto-3'-deoxythymidine 266

A.A.Yuzhakov, Z.G.Chidgeavadze and

R. Sh.Beabealash-villi

Contents continued overleaf ix

Development of non-radioactive methods of nucleic acids hybridization 267

assay on polymer supports of a new type using poly- and oligonucleotide

probesT.I.Vener, M.F.Turchinsky, V.P.Zubov, T.S.Godovikova, T.N.Orlova,V.A.Shamanin and V.F.Kulikova

The hybridase RNA hydrolysis can be altered by oligonucleotide probes 268

N.F.Krynetskaya, V.G.Metelev, V.N.Tashlitski, V.V.Sukhomlinov and

Z.A.Shabarova

Non-nucleotide phosphoramidite reagent for non-radioactive polylabelling 269

of oligo- and polynucleotides

V.A.Korshun, Y.G.Boreskov, N.B.Pestov and Yu.A.Berlin

H-phosphonate oligonucleotide synthesis in solution 270

I.Ya.Dubey, T.V.Lyapina and D.M.Fedoryak

Preparative synthesis of oligodeoxyribonucleotides with a terminal 271

5'-phosphate group

T.V.Abramova, L.V.Gajevaja, V.V.Gorn, G.A.Maksakova, V.P.Slarostin,

V.LJamkovoi and L.V.Vratzkikh

Simple synthesis of triester analogs of oligonucleotides for use as antisense 272

antiviral agents

M.A.Dyadchenko and S.V.Vinogradov

Optimization of synthesis of 5'-porphyrin-oligonucIeotide conjugates 273

and studies of their interaction with eukaryotic cells

A.S.Boutorine, T.Le Doan, J.P.Battioni and C.H61ene

Control of the expression of an early gene of SV40 with natural and 274

modified oligonucleotides

M.L.Capobianco, A.Garbesi, F.Arcamone, B.Maschera and G.Palu

Use of synthetic oligonucleotides for studying gene structure and 275

polymorphism: human genes encoding tumor necrosis factors and their

receptors

R.L.Turetskaya, I.A.Udalova, D.V.Kuprash, A.V.Terskikh

and S.A.Nedospasov

The application of the method of ligation-mediated, single-sided 276

polymerase chain reaction for the analysis of heterogeneity of

S'-untranslated regions of specific mRNA

R.I.Pekhletsky, B.K.Chernov and P.M.Rubtsov

Enzymatic incorporation of fluorescent labels into oligonucleotides 277

L.A.Alexandrova, M.A.Lukin, L.S.Victorova and T.A.Rozovskaya

PCR-mediated analysis of human rotaviruses 278

I.N.Bessarab, N.A.Novikova and A.M.Borodin

x

T4 DNA ligase distinguishes between Rp- and Sp- configurations at 279

phosphorus chiral atom on phosphoramide DNA analogs

E.V.Shibanova, V.G.Korobko and V.N.Dobrynin

Synthetic deoxyoligonucleotide probes for indentification of flaviviruses 280

V.I.Zlobin, D.A.Drokin and V.A.Shamanin

Fatty radical-modified antisense oligodeoxynucleotides as effective 281

inhibitors of influenza virus reproductionS.V.Vinogradov, V.S.Pheoktistov and A.V.Kabanov

Vector to search for and sequencing of yeast promoters 282

L.Yu.Filippova, I.V.Severtsova and N.M.Zvonok

Specificity of HIV inhibition by modified antisense oligonucleotides 283

T.Abramova, V.Blinov, V.Vlassov, V.Gorn, V.Zarytova, E.Ivanova,

D.Konevets, O.Plyasunova, A.Pokrovsky, L.Sandakhchiev, F.Svinarchuk,

V.Starostin and S.Chaplygina

Direct non-radioactive detection of virus RNA by a novel RNA-PCR test 284

T.S.Godovikova, T.N.Orlova, V.F.Zarytova, V.A.Shamanin,

N.V.Vorobjova, N.A.Serdjukova and A.G.Romashchenko

Interaction of modified oligonucleotides with eukaryotic and mycoplasma 285

cells and their fate inside the cells

A.S.Ryte, N.V.Amirchanov, A.A.Koshkin, M.B.Nechaeva, E.M.Ivanova,

V.F.Zarytova and V.V.Vlassov

New porphyrin-linked oligonucleotide derivatives for sequence-specific 286

chemical modification of DNA

E.I.Frolova, N.LKomorova, E.M.Ivanova, G.P.Ponomariov,

G.N.Kirillova and V.V.Vlassov

Application of synthetic oligonucleotides to create a vector for human 287

gamma-interferon expression in mammary gland

V.N.Dobrovolsky and O.A.Larionov

Synthesis and purification of thio-oligonucleotides 288

M.Bengtstrom and L.Paulin

Synthesis and purification of biotinylated oligonucleotides 289

M.Bengtstrom and L.Paulin

2'-5'-linked oligonucleotides form stable complexes with complementary 290

RNA and DNA

M.J.Damha, P.A.Giannaris and N.Khan

Synthesis of oligonucleotides containing 3-deaza-2'-deoxyadenosine. 291

Interaction of the oligonucleotides with the drug distamycin A

R.Cosstick and C.Lever

Contents continued overleaf XI

Synthesis of cross-linked nucleosides as potential inhibitors of thymidine 292

kinase

R.Cosstick and S.Z.Nayyar

Synthetic RNA in the study of RNA-protein interactions of MS2 293

bacteriophage

S.T.S.Goodman, S.J.Talbot, I.Haneef, H.K.Tewary, C.W.G.Fishwick and

P.G.Stockley

Recombinant human interleukin 4. H-phosphonate synthesis of 294

structural gene, expression in E.coli, isolation and study of chemical and

biological propertiesA.Kurkin, M.Coulagina, N.Batchikova, V.Smirnov, S.Lutsenko

and A.Azhayev

Synthesis, solution conformations and hydrolytic stability of 3-substituted 295

2'-deoxyribonucleosides

S.Zavgorodny, M.Polianski, V.Kriukov, P.Oksman, H.Hakala, H.Lonnberg,A.Van Aerschot, P.Herdewijn and A.Azhayev

Investigation into the use of very short oligonucleotide probes for 296

identifying DNA and RNA sequences containing characteristic d(AT) and

AU motifs

C.Blonski, C.Carillon, B.Delpech, B.Pessegue\ P.Chalon and D.Shire

Solid phase synthesis of small circular DNA 297

L.De Napoli, L.Mayol, G.Piccialli and C.Santacroce

Liquid phase synthesis and evaluation of antisense oligodeoxynucleotides 298

to DNA polymerase a

M.Mazzei, A.Balbi, E.Sottofattori, T.Abramova, A.Alama and A.Nicolin

Characterization of uptake, degradation and toxicity of antisense ODNs 299

in cancer cells

S.Capaccioli, A.Quattrone, G.Basi, N.Schiavone and C.Giannini

General method for site-directed mutagenesis and cloning of synthetic 300

single-stranded DNA in circular vectors

V.L.Drutsa and V.R.Kaberdin

Suppression of influenza virus biopolymers functions and reproduction 301

of the virus by oligodeoxynucleotide derivatives

L.V.Yurchenko, T.V.Abramova, E.M.Ivanova, G.A.Nevinsky,

N.Y.Nomokonova, T.N.Fokina and V.V.Vlassov

DNA in chromatin is available for sequence-specific chemical modification 302

with oligonucleotide derivatives

N.D.Kobets, E.L.Chernolovskaya, R.G.Borissov, A.V.Gorozhankin,E.M.Ivanova and V.V.Vlassov

xn

Selectivity of the sequence specific alkylation of high molecular weight 303

RNA

M.A.Zenkova, G.G.Karpova, A.S.Levina and S.V.Mamaev

The periodic system of DNA restriction-modification sites 304

V.Yu.Shumilov

Preparative synthesis of short oligoribonucleotide by immobilized 305

RNA ligase of T4 bacteriophage

A.G.Venyaminova, L.V.Vratskikh, M.N.Repkova and V.I.Yamkovoy

Plasmid vectors for 'unclonable' DNA constructions 306

S.V.Reverdatto, V.A.Beilinson, A.F.Fradkov, N.N.Polushin and

V.A.Efimov

DNA duplexes with non-nucleotide inserts: interaction with restriction 308

endonucleases

E.A.Kubareva, O.V.Petrauskene, A.S.Karyagina, I.I.Nikolskaya and

E.S.Gromova

A simple and low cost DNA amplifier 309

Yu.G.Boreskov

Cloning and transcription the DNA copies of autocatalytic RNA rql3S 310

and rql34E.Avota, J.Vishnevsky, A.Skangals and V.Berzin

Interaction of oligonucleotides with cellular receptors 311

L.Yakubov, L.Yurchenko, M.Nechaeva, E.Rykova, V.Karamyshev,

J.Tonkinson, V.Vlassov and C.A.Stein

Affinity modification of chromatin proteins located near open oligo(dA), 312

Oligo(dTG) and Alu- DNA sequences

E.L.Chernolovskaya, R.G.Borissov, A.V.Gorodjankin, E.M.Ivanova,

N.D.Kobets and V.V.Vlassov

The use of polymerase chain reaction for the detection of Herpes simplex 313

virus type 1 and 2

I.V.Alexuk, S.V.Vinogradov and V.I.Kiselev

Synthesis of an artificial gene for the albumin binding domain of 314

streptococcal protein G

D.Foti, N.N.Polushin, O.G.Chakhmakhcheva and V.A.Efimov

C-fos gene expression in spontaneously transformed mouse fibroblast 315

cell lines

Y.V.Lavrovsky, F.P.Svinarchuk, V.A.Lavrovsky, D.A.Konevetz and

V.V.Vlassov

Nuclear peptides specifically interacting with oligonucleotides 316

F.P.Svinarchuk, Y.V.Lavrovsky, D.A.Konevets and V.V.Vlassov

Contents continued overleaf xiii

Identification of the sickle-cell anemia mutation by means of the 317

PCR-mediated mismatch-dependent primer extension

K.R.Birikh, O.V.Plutalov, E.I.Schwartz and Yu.A.Berlin

Oligonucleotide synthesis and multiplex DNA sequencing using 318

chemiluminescent detection

H.Koster, S.Beck, J.M.Coull, T.Dunne, B.D.Gildea, C.Kissinger and

Th.O'Keefe

Author index 323

xiv