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M061040

Sigma-Aldrich

Phosphate-ON Phosphoramidite

configured for MerMade

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Synonym(s):
Phosphate-ON amidite
Empirical Formula (Hill Notation):
C49H62N7O11P
Molecular Weight:
956.03
MDL number:
PubChem Substance ID:
NACRES:
NA.21

type

for DNA synthesis

product line

Proligo Reagents

Assay

≥98% (31P-NMR)
≥98.0% (reversed phase HPLC)

compatibility

configured for MerMade

storage temp.

−20°C

SMILES string

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

InChI

1S/C49H62N7O11P/c1-33(2)56(34(3)4)68(64-28-11-24-50)67-41(23-25-51)29-44(57)52-26-12-27-53-48(60)66-42-30-45(55-31-35(5)46(58)54-47(55)59)65-43(42)32-63-49(36-13-9-8-10-14-36,37-15-19-39(61-6)20-16-37)38-17-21-40(62-7)22-18-38/h8-10,13-22,31,33-34,41-43,45H,11-12,23,26-30,32H2,1-7H3,(H,52,57)(H,53,60)(H,54,58,59)/t41-,42+,43-,45-,68?/m1/s1

InChI key

MCGIOYZUTKDSIL-NNUNARBDSA-N

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General description

Phosphate-ON phosphoramidite is a chemical phosphorylation reagent that can be employed to introduce a phosphate group at the 5′ terminus of an oligonucleotide. Chemical phosphorylation is a cost-effective alternative to enzymatic phosphorylation methods, allowing the introduction of terminal phosphate groups in high yields, at any desired scale. We offer Phosphate-ON phosphoramidite in powder form, enabling the dissolution of the reagent in acetonitrile to be easily monitored.

Application

The application of Phosphate-ON Phosphoramidite is fully compatible with standard cleavage and deprotection procedures at the end of oligonucleotide synthesis. Phosphate-ON phosphoramidite comprises a thymidine nucleoside, which is removed from the oligonucleotide during the cleavage and deprotection process.

Other Notes

The key features of Phosphate-ON Phosphoramidite are as follows:
  • Powder format enables dissolution to be easily monitored and facilitatesproduct handling
  • Fully compatible with standard phosphoramidite reagents and synthesisconditions
  • Compatible with dG(dmf) fast deprotection chemistry: the oligonucleotidecan be cleaved from the support and deprotected in concentratedammonia at 55 °C in only 2 hours
  • Comprises a DMT-group for trityl monitoring
  • Dissolves easily in acetonitrile to a 0.1 M solution
  • High coupling efficiency of ≥98.0% under standard DNA phosphoramiditecoupling conditions
  • Cleavage of both phosphate protective groups through a β-eliminationprocess

Legal Information

This product is covered under US Patent Number 7,276,598

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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