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A211140

Sigma-Aldrich

DMT-2′O-Methyl-rA(bz) Phosphoramidite

configured for MerMade

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Synonym(s):
DMT-2′-O-Me-rA(bz) amidite, N-benzoyl-5′-O-[bis(4-methoxyphenyl)phenylmethyl]-2′-O-methyl-adenosine, 3′-[2-cyanoethyl N,N-bis(1-methylethyl)phosphoramidite]
Empirical Formula (Hill Notation):
C48H54N7O8P
CAS Number:
Molecular Weight:
887.96
MDL number:
NACRES:
NA.51

biological source

non-animal source (no BSE/TSE risk)

Quality Level

product line

Proligo Reagents

Assay

≥99% (31P-NMR)
≥99.0% (redox titration)

form

powder

impurities

≤0.3% mA2 (reversed phase HPLC, Hydrolysate)
≤0.3% mA3 (reversed phase HPLC, DMT-rA(bz)me)
≤0.3% water content (Karl Fischer)
≤0.5% P(III) Impurities 100-169ppm (31P-NMR)
≤0.5% single Impurity (redox titration)
≤1.0% mA1 (reversed phase HPLC, DMT-rA(bz)me-DMT)
≤3% residual Solvent content

color

white to off-white

suitability

conforms to structure for H-NMR
conforms to structure for LC-MS

compatibility

configured for MerMade

storage temp.

2-8°C

SMILES string

CO[C@@H]1[C@H](OP(OCCC#N)N(C(C)C)C(C)C)[C@@H](COC(c2ccccc2)(c3ccc(OC)cc3)c4ccc(OC)cc4)O[C@H]1n5cnc6c(NC(=O)c7ccccc7)ncnc56

InChI

1S/C48H54N7O8P/c1-32(2)55(33(3)4)64(61-28-14-27-49)63-42-40(62-47(43(42)59-7)54-31-52-41-44(50-30-51-45(41)54)53-46(56)34-15-10-8-11-16-34)29-60-48(35-17-12-9-13-18-35,36-19-23-38(57-5)24-20-36)37-21-25-39(58-6)26-22-37/h8-13,15-26,30-33,40,42-43,47H,14,28-29H2,1-7H3,(H,50,51,53,56)/t40-,42-,43-,47-,64?/m1/s1

InChI key

AZCGOTUYEPXHMJ-PSVHYZMASA-N

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General description

Proligo′s 2′O-Methyl RNA monomers are compatible with fast deprotectionschemes that are based on the application of aliphatic amines, such asmethylamine. The adenosine and guanosine monomers are protected bythe standard benzoyl (bz) and isobutyryl (ib) groups.2′O-Methyl RNA is a nucleic acid analog that is characterized by theexceptional hybridization properties that it imparts with complimentaryDNA or RNA, as well as increased stability against enzymatic degradationcompared to natural nucleic acids.The unique combination of properties of 2′O-Methyl RNA had foundwidespread use in the fields of:
  • Diagnostic probes
  • Aptamer and ribozyme development
  • Mixed 2′O-Methyl-RNA/DNA antisense molecules

Features and Benefits

  • High yield of crude oligonucleotides
  • Compatible with DNA synthesis
  • Can be employed together with DNA or RNA phosphoramidites in thesame synthesis to produce mixmer oligonucleotides
  • Recommended deprotection conditions are 8 hours at 55 °C usingconcentrated ammonia solution, or with AMA (concentrated ammonia/40% aqueous methylamine I/I, v/v) for 10 minutes at 65 °C
  • Purification and other downstream processing of fully modified 2′OMethyl RNA oligonucleotides are simpler than in the case of RNA, as nospecial precautions are required to provide protection against nucleolyticdegradationDMT-2′O-Methyl-rA(bz) Phosphoramidite is configured for MerMade Synthesizers.

Other Notes

The synthesis cycle for 2′O-Methyloligoribonucleotides consists of the sameseries of reactions as the cycle that is employed for DNA monomers.However, the rate of coupling for 2′O-Methyl RNA monomers is slowercompared to that of DNA monomers (a coupling time of 6 minutes isrecommended for 2′O-Methyl RNA monomers compared to 90 seconds forDNA monomers). With the exception of the 2′O-Methyl RNA monomers andsupports, RNA synthesis is accomplished with the same reagents as DNAsynthesis. All 2′O-Methyl RNA phosphoramidites from Sigma-Aldrich arediluted with dry acetonitrile.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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