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722332

Sigma-Aldrich

6-Amino-7-deazapurine

97%

Synonym(s):

4-Amino-7H-pyrrolo[2,3-d]pyrimidine

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About This Item

Empirical Formula (Hill Notation):
C6H6N4
CAS Number:
1500-85-2
Molecular Weight:
134.14
MDL number:
MFCD01686848
UNSPSC Code:
12352005
PubChem Substance ID:
329763917
NACRES:
NA.22

Assay

97%

form

solid

mp

257-262 °C

SMILES string

Nc1ncnc2[nH]ccc12

InChI

1S/C6H6N4/c7-5-4-1-2-8-6(4)10-3-9-5/h1-3H,(H3,7,8,9,10)

InChI key

PEHVGBZKEYRQSX-UHFFFAOYSA-N

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301

Precautionary Statements

P301 + P310

Hazard Classifications

Acute Tox. 3 Oral

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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Munmun Maiti et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 18(3), 857-868 (2011-12-17)
Nucleoside phosphoramidates (NPs) are a class of nucleotide analogues that has been developed as potential antiviral/antitumor prodrugs. Recently, we have shown that some amino acid nucleoside phosphoramidates (aaNPs) can act as substrates for viral polymerases like HIV-1 RT. Herein, we report
A Ono et al.
Nucleic acids research, 12(23), 8939-8949 (1984-12-11)
Deoxydecanucleotides having a recognition sequence of Bgl II and Sau 3AI, and their 7-deazaadenine analogs were synthesized. The decanucleotides containing 7-deazaadenine in place of adenine were partially resistant to the hydrolysis by Sau 3AI and strongly resistant to that by
Akimitsu Okamoto et al.
Bioorganic & medicinal chemistry letters, 12(1), 97-99 (2001-12-12)
2-Amino-7-deazaadenine ((AD)A) was incorporated into oligodeoxynucleotides (ODN) and their base-pairing properties with natural nucleobases were investigated. In melting temperature (T(m)) experiments, the duplex containing an (AD)A/C base pair showed a high stability comparable to that containing (AD)A/T base pair. Destabilization
Pavel Kielkowski et al.
The Journal of organic chemistry, 76(9), 3457-3462 (2011-03-24)
(Cytosin-5-yl)ethynyl derivatives of pyrimidine and 7-deazaadenine 2-deoxyribonucleosides and nucleoside triphosphates (dNTPs) were prepared in one step by the aqueous Sonogashira coupling of unprotected halogenated nucleos(t)ides with 5-ethynylcytosine. The modified dNTPs were good substrates for DNA polymerases suitable for primer extension
Jennifer D Tibodeau et al.
Inorganic chemistry, 43(2), 408-410 (2004-01-21)
The effect of DNA bending on nucleobase electron transfer was investigated by studying the oxidation of double-stranded sequences containing seven repeats of the known bent sequence d(GGCA(1)A(2)A(3)A(4)A(5)A(6)C) where 7-deazaadenine (zA) was substituted at the A(3) position. Native gel electrophoresis was
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