IL99261A - Methods for the synthesis of oligonucleotides with codon triplets with random codon pairs - Google Patents

Methods for the synthesis of oligonucleotides with codon triplets with random codon pairs

Info

Publication number: IL99261A
Authority: IL; Israel
Prior art keywords: codon; codons; column; synthesis; oligonucleotides
Prior art date: 1990-08-24

Application number

IL9926191A

Other languages

English (en)

Hebrew (he)

Other versions

IL99261A0 (en

Original Assignee

Ixsys Inc

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1990-08-24

Filing date

1991-08-21

Publication date

1996-09-12

1991-08-21 Application filed by Ixsys Inc filed Critical Ixsys Inc

1992-07-15 Publication of IL99261A0 publication Critical patent/IL99261A0/xx

1996-09-12 Publication of IL99261A publication Critical patent/IL99261A/en

Links

108091034117 Oligonucleotide Proteins 0.000 title claims abstract description 99
JLCPHMBAVCMARE-UHFFFAOYSA-N [3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methyl [5-(6-aminopurin-9-yl)-2-(hydroxymethyl)oxolan-3-yl] hydrogen phosphate Polymers Cc1cn(C2CC(OP(O)(=O)OCC3OC(CC3OP(O)(=O)OCC3OC(CC3O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c3nc(N)[nH]c4=O)C(COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3CO)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cc(C)c(=O)[nH]c3=O)n3cc(C)c(=O)[nH]c3=O)n3ccc(N)nc3=O)n3cc(C)c(=O)[nH]c3=O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)O2)c(=O)[nH]c1=O JLCPHMBAVCMARE-UHFFFAOYSA-N 0.000 title claims abstract description 69
238000000034 method Methods 0.000 title claims abstract description 53
230000002194 synthesizing effect Effects 0.000 title claims abstract description 18
108020004705 Codon Proteins 0.000 title description 174
238000006243 chemical reaction Methods 0.000 claims abstract description 92
239000000178 monomer Substances 0.000 claims abstract description 89
238000005859 coupling reaction Methods 0.000 claims abstract description 46
230000008878 coupling Effects 0.000 claims abstract description 31
238000010168 coupling process Methods 0.000 claims abstract description 31
238000002156 mixing Methods 0.000 claims abstract description 21
239000003795 chemical substances by application Substances 0.000 claims 1
230000015572 biosynthetic process Effects 0.000 description 73
238000003786 synthesis reaction Methods 0.000 description 73
239000011324 bead Substances 0.000 description 29
150000001413 amino acids Chemical class 0.000 description 20
239000002773 nucleotide Substances 0.000 description 19
125000003729 nucleotide group Chemical group 0.000 description 19
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
239000000203 mixture Substances 0.000 description 15
239000007795 chemical reaction product Substances 0.000 description 11
239000000463 material Substances 0.000 description 10
108090000765 processed proteins & peptides Proteins 0.000 description 8
239000000047 product Substances 0.000 description 8
230000002068 genetic effect Effects 0.000 description 7
UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical compound O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 description 7
OPTASPLRGRRNAP-UHFFFAOYSA-N cytosine Chemical compound NC=1C=CNC(=O)N=1 OPTASPLRGRRNAP-UHFFFAOYSA-N 0.000 description 6
239000000725 suspension Substances 0.000 description 6
RWQNBRDOKXIBIV-UHFFFAOYSA-N thymine Chemical compound CC1=CNC(=O)NC1=O RWQNBRDOKXIBIV-UHFFFAOYSA-N 0.000 description 6
238000002515 oligonucleotide synthesis Methods 0.000 description 5
239000011148 porous material Substances 0.000 description 5
102000004196 processed proteins & peptides Human genes 0.000 description 5
239000011521 glass Substances 0.000 description 4
238000012986 modification Methods 0.000 description 4
230000004048 modification Effects 0.000 description 4
229920001184 polypeptide Polymers 0.000 description 4
239000007790 solid phase Substances 0.000 description 4
241000894007 species Species 0.000 description 4
239000013598 vector Substances 0.000 description 4
GFFGJBXGBJISGV-UHFFFAOYSA-N Adenine Chemical compound NC1=NC=NC2=C1N=CN2 GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 description 3
241000024188 Andala Species 0.000 description 3
108020004414 DNA Proteins 0.000 description 3
FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 3
230000000692 anti-sense effect Effects 0.000 description 3
229940104302 cytosine Drugs 0.000 description 3
-1 dimethoxytrityl Chemical group 0.000 description 3
238000009826 distribution Methods 0.000 description 3
239000007788 liquid Substances 0.000 description 3
229930182817 methionine Natural products 0.000 description 3
230000008569 process Effects 0.000 description 3
KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
229930024421 Adenine Natural products 0.000 description 2
NSTPXGARCQOSAU-VIFPVBQESA-N N-formyl-L-phenylalanine Chemical compound O=CN[C@H](C(=O)O)CC1=CC=CC=C1 NSTPXGARCQOSAU-VIFPVBQESA-N 0.000 description 2
108091028043 Nucleic acid sequence Proteins 0.000 description 2
ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 2
229960000643 adenine Drugs 0.000 description 2
238000011166 aliquoting Methods 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
230000008901 benefit Effects 0.000 description 2
239000002981 blocking agent Substances 0.000 description 2
230000003247 decreasing effect Effects 0.000 description 2
239000000539 dimer Substances 0.000 description 2
238000010353 genetic engineering Methods 0.000 description 2
238000010348 incorporation Methods 0.000 description 2
239000006194 liquid suspension Substances 0.000 description 2
238000002703 mutagenesis Methods 0.000 description 2
231100000350 mutagenesis Toxicity 0.000 description 2
238000003752 polymerase chain reaction Methods 0.000 description 2
238000011160 research Methods 0.000 description 2
238000012163 sequencing technique Methods 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
229940113082 thymine Drugs 0.000 description 2
238000013519 translation Methods 0.000 description 2
FMKJUUQOYOHLTF-OWOJBTEDSA-N (e)-4-azaniumylbut-2-enoate Chemical compound NC\C=C\C(O)=O FMKJUUQOYOHLTF-OWOJBTEDSA-N 0.000 description 1
ASJSAQIRZKANQN-CRCLSJGQSA-N 2-deoxy-D-ribose Chemical compound OC[C@@H](O)[C@@H](O)CC=O ASJSAQIRZKANQN-CRCLSJGQSA-N 0.000 description 1
HMFHBZSHGGEWLO-SOOFDHNKSA-N D-ribofuranose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H]1O HMFHBZSHGGEWLO-SOOFDHNKSA-N 0.000 description 1
238000001712 DNA sequencing Methods 0.000 description 1
229930010555 Inosine Natural products 0.000 description 1
UGQMRVRMYYASKQ-KQYNXXCUSA-N Inosine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C2=NC=NC(O)=C2N=C1 UGQMRVRMYYASKQ-KQYNXXCUSA-N 0.000 description 1
108020004485 Nonsense Codon Proteins 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
PYMYPHUHKUWMLA-LMVFSUKVSA-N Ribose Natural products OC[C@@H](O)[C@@H](O)[C@@H](O)C=O PYMYPHUHKUWMLA-LMVFSUKVSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
HMFHBZSHGGEWLO-UHFFFAOYSA-N alpha-D-Furanose-Ribose Natural products OCC1OC(O)C(O)C1O HMFHBZSHGGEWLO-UHFFFAOYSA-N 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
230000003321 amplification Effects 0.000 description 1
239000000074 antisense oligonucleotide Substances 0.000 description 1
238000012230 antisense oligonucleotides Methods 0.000 description 1
238000013459 approach Methods 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
230000000903 blocking effect Effects 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
230000008859 change Effects 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
230000000295 complement effect Effects 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
238000006482 condensation reaction Methods 0.000 description 1
238000012217 deletion Methods 0.000 description 1
230000037430 deletion Effects 0.000 description 1
238000013461 design Methods 0.000 description 1
238000001514 detection method Methods 0.000 description 1
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical group CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
238000009396 hybridization Methods 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
229960003786 inosine Drugs 0.000 description 1
238000003541 multi-stage reaction Methods 0.000 description 1
238000003199 nucleic acid amplification method Methods 0.000 description 1
238000001668 nucleic acid synthesis Methods 0.000 description 1
108020004707 nucleic acids Proteins 0.000 description 1
150000007523 nucleic acids Chemical class 0.000 description 1
102000039446 nucleic acids Human genes 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
150000008300 phosphoramidites Chemical class 0.000 description 1
239000002243 precursor Substances 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
230000000135 prohibitive effect Effects 0.000 description 1
108091008146 restriction endonucleases Proteins 0.000 description 1
230000002441 reversible effect Effects 0.000 description 1
239000000523 sample Substances 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
238000002741 site-directed mutagenesis Methods 0.000 description 1
239000000758 substrate Substances 0.000 description 1
238000001308 synthesis method Methods 0.000 description 1
238000012546 transfer Methods 0.000 description 1
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
239000013638 trimer Substances 0.000 description 1
229940035893 uracil Drugs 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H21/00—Compounds containing two or more mononucleotide units having separate phosphate or polyphosphate groups linked by saccharide radicals of nucleoside groups, e.g. nucleic acids

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Biochemistry (AREA)
Molecular Biology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Biotechnology (AREA)
General Health & Medical Sciences (AREA)
Genetics & Genomics (AREA)
Saccharide Compounds (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)

IL9926191A 1990-08-24 1991-08-21 Methods for the synthesis of oligonucleotides with codon triplets with random codon pairs IL99261A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US57364890A	1990-08-24	1990-08-24

Publications (2)

Publication Number	Publication Date
IL99261A0 IL99261A0 (en)	1992-07-15
IL99261A true IL99261A (en)	1996-09-12

Family

ID=24292837

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL9926191A IL99261A (en)	1990-08-24	1991-08-21	Methods for the synthesis of oligonucleotides with codon triplets with random codon pairs

Country Status (11)

Country	Link
EP (1)	EP0544809B1 (de)
JP (2)	JP3306063B2 (de)
AT (1)	ATE174598T1 (de)
AU (1)	AU8505191A (de)
CA (1)	CA2089362C (de)
DE (1)	DE69130647T2 (de)
IE (1)	IE66123B1 (de)
IL (1)	IL99261A (de)
NZ (1)	NZ239498A (de)
TW (1)	TW217416B (de)
WO (1)	WO1992003461A1 (de)

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1991
- 1991-08-20 EP EP91916483A patent/EP0544809B1/de not_active Expired - Lifetime
- 1991-08-20 WO PCT/US1991/005939 patent/WO1992003461A1/en not_active Ceased
- 1991-08-20 JP JP51511591A patent/JP3306063B2/ja not_active Expired - Fee Related
- 1991-08-20 AT AT91916483T patent/ATE174598T1/de active
- 1991-08-20 DE DE69130647T patent/DE69130647T2/de not_active Expired - Fee Related
- 1991-08-20 AU AU85051/91A patent/AU8505191A/en not_active Abandoned
- 1991-08-20 CA CA002089362A patent/CA2089362C/en not_active Expired - Fee Related
- 1991-08-21 IL IL9926191A patent/IL99261A/en not_active IP Right Cessation
- 1991-08-22 NZ NZ239498A patent/NZ239498A/en unknown
- 1991-08-23 IE IE299391A patent/IE66123B1/en not_active IP Right Cessation
- 1991-09-26 TW TW080107638A patent/TW217416B/zh active
2001
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Publication number	Publication date
CA2089362A1 (en)	1992-02-25
EP0544809A1 (de)	1993-06-09
EP0544809B1 (de)	1998-12-16
NZ239498A (en)	1993-07-27
DE69130647D1 (de)	1999-01-28
JP2001299342A (ja)	2001-10-30
JP3306063B2 (ja)	2002-07-24
WO1992003461A1 (en)	1992-03-05
EP0544809A4 (en)	1994-08-17
IE912993A1 (en)	1992-02-26
AU8505191A (en)	1992-03-17
IE66123B1 (en)	1995-12-13
TW217416B (de)	1993-12-11
IL99261A0 (en)	1992-07-15
ATE174598T1 (de)	1999-01-15
JPH06503809A (ja)	1994-04-28
CA2089362C (en)	2000-11-21
DE69130647T2 (de)	1999-05-06

Legal Events

Date	Code	Title
1997-02-18	FF	Patent granted
1997-06-10	KB	Patent renewed
1998-01-04	KB	Patent renewed
2001-10-31	KB	Patent renewed
2005-11-20	KB	Patent renewed
2010-10-31	MM9K	Patent not in force due to non-payment of renewal fees

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