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A112000

Sigma-Aldrich

DMT-dA(tac) Phosphoramidite

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Synonym(s):
DMT-dA(tac) amidite
Empirical Formula (Hill Notation):
C52H62N7O8P
CAS Number:
149989-58-2
Molecular Weight:
944.06
MDL number:
MFCD00058443
UNSPSC Code:
12352200
PubChem Substance ID:
329770670
NACRES:
NA.51

type

for DNA synthesis

Quality Level

200

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

storage temp.

−20°C

SMILES string

COc1ccc(cc1)C(OC[C@H]2O[C@H](C[C@@H]2OP(OCCC#N)N(C(C)C)C(C)C)n3cnc4c(NC(=O)COc5ccccc5)ncnc34)(c6ccccc6)c7ccc(OC)cc7

InChI

1S/C48H54N7O8P/c1-33(2)55(34(3)4)64(61-27-13-26-49)63-41-28-44(54-32-52-45-46(50-31-51-47(45)54)53-43(56)30-59-40-16-11-8-12-17-40)62-42(41)29-60-48(35-14-9-7-10-15-35,36-18-22-38(57-5)23-19-36)37-20-24-39(58-6)25-21-37/h7-12,14-25,31-34,41-42,44H,13,27-30H2,1-6H3,(H,50,51,53,56)/t41-,42+,44+,64?/m0/s1

InChI key

INUFZOANRLMUCW-SDNJGBRXSA-N

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General description

DMT-dA(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 baselabile monomers and reporters as well as in-situ synthesis schemes on glass surfaces.

Key Features of TAC Chemistry are -

  • Deprotection of the TAC group is ultra-fast: complete deprotection in concentrated ammonia occurs within 15 minutes at 55 °C or two hours at room temperature
  • Compatible with the AMA deprotection reagent (a mixture of ≥25% ammonia in water with 40% aqueous methylamine I/I, v/v)
  • Highly soluble in acetonitrile. No need to add co-solvents such as dimethylformamide or methylene chloride
  • Suitable for the synthesis of oligomers with base-labile units e.g., dyes and modifiers, because of less exposure to ammonia and the possibility of room temperature deprotection
  • No change is required in the reagents commonly used for DNA synthesis, except that Proligo′s Fast Deprotection Cap A solution is used instead of Cap A solution •
  • The application of dA(tac) minimizes depurination and improves the quality of oligonucleotides

Features and Benefits

  • 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.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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