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U211050

Sigma-Aldrich

DMT-2′O-TBDMS-rU Phosphoramidite

configured for ÄKTA® and OligoPilot®

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Synonym(s):
5′-O-[bis(4-methoxyphenyl)phenylmethyl]-2′-O-[(1,1-dimethylethyl)dimethylsilyl]-uridine, 3′-[2-cyanoethyl N,N-bis(1-methylethyl)phosphoramidite], DMT-2′-O-TBDMS-rU amidite
Empirical Formula (Hill Notation):
C45H61N4O9PSi
CAS Number:
118362-03-1
Molecular Weight:
861.05
MDL number:
MFCD00080343
UNSPSC Code:
12352200
PubChem Substance ID:
329827600
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

technique(s)

oligo synthesis: suitable

impurities

≤0.3% water content (Karl Fischer)
≤0.5% P(III) Impurities 100-169ppm (31P-NMR)
≤0.5% single Impurity (reversed phase HPLC)
≤3% 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

compatibility

configured for ÄKTA® and OligoPilot®

nucleoside profile

base: uridine
base protecting group: none
2' protecting group: TBDMS
5' protecting group: DMT
deprotection: fast/standard

storage temp.

−20°C

SMILES string

COc1ccc(cc1)C(OC[C@H]2O[C@H]([C@H](O[Si](C)(C)C(C)(C)C)[C@@H]2OP(OCCC#N)N(C(C)C)C(C)C)N3C=CC(=O)NC3=O)(c4ccccc4)c5ccc(OC)cc5

InChI

1S/C45H61N4O9PSi/c1-31(2)49(32(3)4)59(55-29-15-27-46)57-40-38(56-42(48-28-26-39(50)47-43(48)51)41(40)58-60(10,11)44(5,6)7)30-54-45(33-16-13-12-14-17-33,34-18-22-36(52-8)23-19-34)35-20-24-37(53-9)25-21-35/h12-14,16-26,28,31-32,38,40-42H,15,29-30H2,1-11H3,(H,47,50,51)/t38-,40-,41-,42-,59?/m1/s1

InChI key

SKNLXHRBXYGJOC-ZMHKPELYSA-N

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General description

RNA phosphoramidites, along with RNA CPG, and analogous to DNA synthesis support the synthesis of sequence-specific RNA oligonucleotides for RNA interference (RNAi) and can be used in target validation and other drug development techniques.Modern phosphoramidite-mediated synthesis has enabled routine high-yielding preparations of RNA oligonucleotides. High-quality RNA phosphoramidites are key to low failure rates, the high biological activity of synthesis products, and cost-effectiveness.Key Features:

  • Industry-standard 2′O-TBDMS protective group
  • Consistent lot-to-lot purity and performance
  • Compatible with deprotection methods based on methylamine or AMA
  • Standard RNA phosphoramidites provide excellent coupling results whenused with ETT or BTT as an activator; best results are obtained withActivator 42
  • Capping with standard acetic anhydride capping reagent rather than withFast Deprotection Cap A
  • Manufactured under a certified ISO 9001 quality systemDMT-2′O-TBDMS-rU Phosphoramidite is configured for ABI™ Synthesizers.

Other Notes

RNA monomers feature hydroxyl groups at the 2′-position. In order toprevent the formation of unnatural 2′-5′ phosphordiester bonds duringchain elongation, the 2′OH group is protected with a trialkyl-silyl group, tertbutyldimethylsilyl (TBDMS). The TBDMS group is stable under the acidicconditions used to remove the DMT group during the synthesis cycle, butcan be removed by a variety of methods after cleavage and deprotection ofthe RNA oligomer, e.g., with a solution of tetrabutylammonium fluoride(TBAF) in tetrahydrofurane (THF) or with triethylamine hydrofluoride.

Legal Information

ABI is a trademark of Applera Corporation or its subsidiaries in the US and/or certain other countries
OligoPilot is a registered trademark of Cytiva
ÄKTA is a registered trademark of Cytiva

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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