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C112000

Sigma-Aldrich

DMT-dC(tac) Phosphoramidite

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Synonym(s):
DMT-dC(tac) amidite, N-[2-[4-(1,1-dimethylethyl)phenoxy]acetyl]-5′-O-[bis(4-methoxyphenyl)phenylmethyl]-2′-deoxycytidine, 3′-[2-cyanoethyl N,N-bis(1-methylethyl)phosphoramidite]
Empirical Formula (Hill Notation):
C51H62N5O9P
CAS Number:
Molecular Weight:
920.04

type

for DNA synthesis

Quality Level

product line

Proligo Reagents

Assay

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

form

powder

technique(s)

oligo synthesis: suitable

λ

conforms (UV/VIS Identity)

nucleoside profile

base: deoxycytidine
base protecting group: TAC
2' protecting group: none
5' protecting group: DMT
deprotection: fast

storage temp.

−20°C

SMILES string

CC(C)N(C(C)C)P(OCCC#N)O[C@H]1C[C@@H](O[C@@H]1COC(c2ccccc2)(c3ccccc3)c4ccccc4)N5C=CC(NC(=O)COc6ccc(cc6)C(C)(C)C)=NC5=O

InChI

1S/C49H58N5O7P/c1-35(2)54(36(3)4)62(59-31-17-29-50)61-42-32-46(53-30-28-44(52-47(53)56)51-45(55)34-57-41-26-24-37(25-27-41)48(5,6)7)60-43(42)33-58-49(38-18-11-8-12-19-38,39-20-13-9-14-21-39)40-22-15-10-16-23-40/h8-16,18-28,30,35-36,42-43,46H,17,31-34H2,1-7H3,(H,51,52,55,56)/t42-,43+,46+,62?/m0/s1

InChI key

NHKNJNORWFDRBB-ROEGVEHFSA-N

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General description

DMT-dC(tac) Phosphoramidite is a TAC Protected Phosphoramidite. Substitution of standard protecting groups with the labile TAC (tert.-butylphenoxyacetyl) protecting group results in ultra-fast and easy deprotection under mild conditions, suitable for oligonucleotides with base labile monomers and reporters as well as in-situ synthesis schemes on glass surfaces.

Other Notes

  • The deprotection of oligonucleotide synthesis products with the AMAreagent is ultra-fast: complete deprotection requires 10 minutes at 65 °C
  • Side reactions at C-monomers through transamination are eliminated
  • Not compatible with some base-labile modified nucleosides
  • dC(tac)-phosphoramidite can directly substitute for dC(bz)-phosphoramidite
  • No change is required in the reagents commonly used for DNA synthesis.Acetonitrile is used to dissolve phosphoramidite. The standard aceticanhydride capping reagent can be employed.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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