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G211100

Sigma-Aldrich

DMT-2′O-Methyl-rG(ib) Phosphoramidite

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Synonym(s):
DMT-2′-O-Me-rG(ib) amidite, N-(2-methyl-1-oxopropyl)-5′-O-[bis(4-methoxyphenyl)phenylmethyl]-2′-O-methyl-guanosine, 3′-[2-cyanoethyl N,N-bis(1-methylethyl)phosphoramidite]
Empirical Formula (Hill Notation):
C45H56N7O9P
CAS Number:
Molecular Weight:
869.94
MDL number:
PubChem Substance ID:
NACRES:
NA.51

biological source

non-animal source (no BSE/TSE risk)

Quality Level

Assay

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

form

powder

impurities

≤0.1% single unspecified Impurity (reversed phase HPLC)
≤0.3% mG2 (reversed phase HPLC, Hydrolysate)
≤0.3% mG3 (reversed phase HPLC, DMT-rG(ib)me)
≤0.3 wt. % water content (Karl Fischer)
≤0.5% P(III) Impurities 100-169ppm (31P-NMR)
≤1.0% mG1 (reversed phase HPLC, DMT-rG(ib)me-DMT)
≤3 wt. % residual Solvent content

color

white to off-white

λ

conforms (UV/VIS Identity)

suitability

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

nucleoside profile

base: guanosine
base protecting group: isobutyryl
2' protecting group: methyl
5' protecting group: DMT
deprotection: standard

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(=O)NC(NC(=O)C(C)C)=Nc56

InChI

1S/C45H56N7O9P/c1-28(2)41(53)49-44-48-40-37(42(54)50-44)47-27-51(40)43-39(57-9)38(61-62(59-25-13-24-46)52(29(3)4)30(5)6)36(60-43)26-58-45(31-14-11-10-12-15-31,32-16-20-34(55-7)21-17-32)33-18-22-35(56-8)23-19-33/h10-12,14-23,27-30,36,38-39,43H,13,25-26H2,1-9H3,(H2,48,49,50,53,54)/t36-,38-,39-,43-,62?/m1/s1

InChI key

IRRDHRZUOZNWDJ-MLLDKZSOSA-N

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This Item
G211130G211150A211100
form

powder

form

powder

form

powder

form

powder

assay

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

assay

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

assay

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

assay

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

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

color

white to off-white

color

white to off-white

color

white to off-white

color

white to off-white

impurities

≤0.1% single unspecified Impurity (reversed phase HPLC), ≤0.3% mG3 (reversed phase HPLC, DMT-rG(ib)me), ≤0.5% P(III) Impurities 100-169ppm (31P-NMR), ≤3 wt. % residual Solvent content, ≤0.3% mG2 (reversed phase HPLC, Hydrolysate), ≤1.0% mG1 (reversed phase HPLC, DMT-rG(ib)me-DMT), ≤0.3 wt. % water content (Karl Fischer)

impurities

≤0.1% single unspecified Impurity (reversed phase HPLC), ≤0.3% mG2 (reversed phase HPLC, Hydrolysate), ≤0.3% mG3 (reversed phase HPLC, DMT-rG(ib)me), ≤0.3% water content (Karl Fischer), ≤0.5% P(III) Impurities 100-169ppm (31P-NMR), ≤1.0% mG1 (reversed phase HPLC, DMT-rG(ib)me-DMT), ≤3% residual Solvent content

impurities

≤0.1% single unspecified Impurity (reversed phase HPLC), ≤0.3% mG2 (reversed phase HPLC, Hydrolysate), ≤0.3% mG3 (reversed phase HPLC, DMT-rG(ib)me), ≤0.3% water content (Karl Fischer), ≤0.5% P(III) Impurities 100-169ppm (31P-NMR), ≤1.0% mG1 (reversed phase HPLC, DMT-rG(ib)me-DMT), ≤3% residual Solvent content

impurities

≤0.1% single unspecified Impurity (reversed phase HPLC), ≤0.3% mA2 (reversed phase HPLC, Hydrolysate), ≤0.3% mA3 (reversed phase HPLC, DMT-rA(bz)me), ≤0.3 wt. % water content (Karl Fischer), ≤0.5% P(III) Impurities 100-169ppm (31P-NMR), ≤1.0% mA1 (reversed phase HPLC, DMT-rA(bz)me-DMT), ≤3 wt. % residual Solvent content

General description

DMT-2′O-Methyl-rG(ib) Phosphoramidite belongs to the group of 2′O-Methyl RNA Phosphoramidites. 2′O-Methyl RNA monomers are compatible with fast deprotection schemes that are based on the application of aliphatic amines, such as methylamine. 2′O-Methyl RNA is a nucleic acid analog that is characterized by the exceptional hybridization properties that it imparts with complementary DNA or RNA, as well as increased stability against enzymatic degradation compared to natural nucleic acids. 2′O-Methyl RNA monomers feature methoxy groups at the 2′-position. The methoxy groups are perfectly stable in all conditions employed in the assembly of oligonucleotides by automated phosphoramidite synthesis, and in all standard alkaline deprotection conditions.

Application

DMT-2′O-Methyl-rG(ib) Phosphoramidite can be advantageously incorporated in nucleic acid probes with RNA or DNA for in-vivo or in-vitro applications to convey nuclease resistance.It has widespread applications in the fields of:
  • Diagnostic probes
  • Aptamer and ribozyme development
  • Mixed 2′O-Methyl-RNA/DNA antisense molecules

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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