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U211140

Sigma-Aldrich

DMT-2′O-Methyl-rU Phosphoramidite

configured for MerMade

Synonym(s):

5′-O-[bis(4-methoxyphenyl)phenylmethyl]-2′-O-methyl-uridine, 3′-[2-cyanoethyl N,N-bis(1-methylethyl)phosphoramidite], DMT-2′O-Methyl-rU amidite

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About This Item

Empirical Formula (Hill Notation):
C40H49N4O9P
CAS Number:
110764-79-9
Molecular Weight:
760.81
MDL number:
MFCD00792626
UNSPSC Code:
41116105
NACRES:
NA.51

biological source

non-animal source (no BSE/TSE risk)

Quality Level

300

product line

Proligo Reagents

Assay

≥99% (31P-NMR)
≥99.0% (reversed phase HPLC)

form

powder

mol wt

760.81 g/mol

impurities

≤0.3% mU2 (reversed phase HPLC, Hydrolysate)
≤0.3% mU3 (reversed phase HPLC, DMT-rme)
≤0.3% water content (Karl Fischer)
≤0.5% P(III) Impurities 100-169ppm (31P-NMR)
≤0.5% single Impurity (redox titration)
≤1.0% mU1 (reversed phase HPLC, DMT-rUme-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]1N5C=CC(=O)NC5=O

InChI

1S/C40H49N4O9P/c1-27(2)44(28(3)4)54(51-25-11-23-41)53-36-34(52-38(37(36)49-7)43-24-22-35(45)42-39(43)46)26-50-40(29-12-9-8-10-13-29,30-14-18-32(47-5)19-15-30)31-16-20-33(48-6)21-17-31/h8-10,12-22,24,27-28,34,36-38H,11,25-26H2,1-7H3,(H,42,45,46)/t34-,36-,37-,38-,54?/m1/s1

InChI key

UVUOJOLPNDCIHL-XKZJCBTISA-N

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General description

DMT-2′O-Methyl-rU Phosphoramidite belongs to the class of 2′O-Methyl RNA Phosphoramidites. Its key features include:
  • High yield of crude oligonucleotides Compatible with DNA synthesis
  • Can be employed together with DNA or RNA phosphoramidites in the same synthesis to produce mixmer oligonucleotides
  • Recommended deprotection conditions are 8 hours at 55 deg C using concentrated ammonia solution, or with AMA (concentrated ammonia/40% aqueous methylamine I/I, v/v) for 10 minutes at 65 deg C
  • Purification and other downstream processing of fully modified 2′OMethyl RNA oligonucleotides are simpler than in the case of RNA, as no special precautions are required to provide protection against nucleolytic degradation
  • Synthesis of 2′O-Methyl RNA oligonucleotides is similar to standard DNA synthesis but requires an elongated coupling time (recommended is 6minutes compared to 90 seconds for DNA monomers)
  • 2′O-Methyl RNA phosphoramidites are also available with fast deprotection chemistry

Application

2′O-Methyl RNA nucleoside including DMT-2′O-Methyl-rU Phosphoramidite can be advantageously incorporated in nucleic acid probes with RNA or DNA for in-vivo or in-vitro applications to convey nuclease resistance.The unique combination of properties of 2′O-Methyl RNA had found widespread use in the fields of:

  • Diagnostic probes
  • Aptamer and ribozyme development
  • Mixed 2′O-Methyl-RNA/DNA antisense molecules

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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