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A11100P

Sigma-Aldrich

DMT-dA(bz) Pharmadite®

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Synonym(s):
Adenosine, N-benzoyl-5′-O-[bis(4-methoxyphenyl)phenylmethyl]-2′-deoxy-, 3′-[2-cyanoethyl N,N-bis(1-methylethyl)phosphoramidite], Adenosine, N-benzoyl-5′-O-[bis(4-methoxyphenyl)phenylmethyl]-2′-deoxy-, 3′-[2-cyanoethyl bis(1-methylethyl)phosphoramidite], DMT-dA(bz) Phosphoramidite, N-benzoyl-5′-O-[bis(4-methoxyphenyl)phenylmethyl]-2′-deoxyadenosine, 3′-[2-cyanoethyl N,N-bis(1-methylethyl)phosphoramidite], N6-Benzoyl-5′-O-(4,4′-dimethoxytrityl)-2′-deoxyadenosine-3′-O-[O-(2-cyanoethyl)-N,N′-diisopropylphosphoramidite]
Empirical Formula (Hill Notation):
C47H52N7O7P
CAS Number:
Molecular Weight:
857.93
MDL number:
PubChem Substance ID:
NACRES:
NA.51

biological source

non-animal source (no BSE/TSE risk)

Quality Level

type

for DNA synthesis

product line

Proligo Reagents

Assay

≥99.5% (reversed phase HPLC)
>99.5% (31P-NMR)

form

powder or granules

technique(s)

oligo synthesis: suitable

impurities

>= 170ppm, none detected (S/N <2.5)
≤0.1% P(III) 100-169ppm (31P-NMR)
≤0.1% single unspecified Imprity (reversed phase HPLC)
≤0.3% dA2 (reversed phase HPLC, DMT-dA(bz) cyanoethyl-H-posphonate)
≤0.3% dA3 (reversed phase HPLC, DMT-dA(bz) phosphoramidate)
≤0.30 wt. % water content (Karl Fischer)
≤0.5% P(V) -25-99ppm (31P-NMR)
≤3.0 wt. % residual solvent content

color

white to off-white

solubility

soluble, clear

suitability

conforms to structure for H-NMR
conforms to structure for LC-MS

nucleoside profile

base: deoxyadenosine
base protecting group: benzoyl
2' protecting group: none
5' protecting group: DMT
deprotection: standard

storage temp.

2-8°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)c5ccccc5)ncnc34)(c6ccccc6)c7ccc(OC)cc7

InChI

1S/C47H52N7O7P/c1-32(2)54(33(3)4)62(59-27-13-26-48)61-40-28-42(53-31-51-43-44(49-30-50-45(43)53)52-46(55)34-14-9-7-10-15-34)60-41(40)29-58-47(35-16-11-8-12-17-35,36-18-22-38(56-5)23-19-36)37-20-24-39(57-6)25-21-37/h7-12,14-25,30-33,40-42H,13,27-29H2,1-6H3,(H,49,50,52,55)/t40-,41+,42+,62?/m0/s1

InChI key

GGDNKEQZFSTIMJ-AKWFTNRHSA-N

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General description

DMT-dA(bz) Pharmadite® is a Pharmadite® product line that represents a new class of standard protected DNA phosphoramidites that are designed with highly controlled impurity profiles and exceptional overall purity. Pharmadite phosphoramidites are characterized by their exceptional purity and well-defined impurity profile. In particular, they are essentially free from contaminants that interfere in coupling reactions, such as other nucleosidic or non-nucleosidic phosphoramidites (P(III)-contaminants). All remaining impurities in Pharmadite phosphopramidites, if present, are identified, characterized, and quantified. The impact of any such defined impurities on the synthesis of oligonucleotides is well understood and has been shown to be insignificant.

Application

Pharmadite products fulfill all requirements of starting materials for themanufacture of active pharmaceutical ingredients as defined in the EMEA "Note for guidance on the chemistry of the new active substance," making them suitable building blocks for oligonucleotide drugs.

Other Notes

Pharmadite phosphoramidites are manufactured in scales of up to multi-hundred kilos, under certified ISO 9001 quality systems.

Legal Information

Pharmadite is a registered trademark of Merck KGaA, Darmstadt, Germany

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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