A112000

DMT-dA(tac) Phosphoramidite

• 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

Properties

• type: for DNA synthesis
• 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.: -10 to -25°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

Description

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.

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable