Nucleotide Analogs - Jena Bioscience

Nucleotide Analogs
48
Halogen containing
Nucleotides
Adenosine Nucleotides
2’I-ADP
2’-Iodo-adenosine-5’-diphosphate, Sodium salt
Cat. No. Amount (Units) Price (€)
NU-109S 30 75,--
NU-109L 150 300,--
Molecular Formula: C 10 H 12 N 5 O 9 P 2 I (Anion)
Molecular Weight: 535.08 (Anion)
O O
P P
HO O
O O
2 Na
2’Br-ADP
O
O
OH I
N
N
NH 2
2’-Bromo-adenosine-5’-diphosphate, Sodium salt
Cat. No. Amount (Units) Price (€)
NU-110S 30 75,--
NU-110L 150 300,--
Molecular Formula: C 10 H 12 N 5 O 9 P 2 Br (Anion)
Molecular Weight: 488.08 (Anion)
O O
P P
HO O
O O
2 Na
O
O
OH Br
N
N
N
N
N
NH 2
N
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For solution of the macromolecular phase problem in protein crystallography,
the most commonly used methods (multiple isomorphous replacement (MIR)
and that of multiple wavelength anomalous dispersion (MAD)) still involve the
incorporation of heavy atoms into protein crystals. After crystallization, fi nding
such derivatives is the second major bottle neck in the determination of the
3D structure of bio-macromolecules. Most labelling procedures focus on the
protein itself in a “trial and error“ fashion. Halogenated ATP and GTP analogs,
however, provide an alternative method that allows rational incorporation of
heavy atoms into a large number of physiologically relevant enzymes.
On the other hand, the availability of a suitable leaving group, such as iodine,
opens a way to a straightforward introduction of functional groups for the
synthesis of novel nucleotide analogs.
8I-ADP
8-Iodo-adenosine-5’-diphosphate, Sodium salt
Cat. No. Amount (Units) Price (€)
NU-111S 50 75,--
NU-111L 250 300,--
Molecular Formula: C 10 H 12 N 5 O 10 P 2 I (Anion)
Molecular Weight: 551.08 (Anion)
O O
P P
HO O
O O
2 Na
8Br-ADP
O
I
O
OH OH
N
N
NH 2
8-Bromo-adenosine-5’-diphosphate, Sodium salt
Cat. No. Amount (Units) Price (€)
NU-112S 100 75,--
NU-112L 500 300,--
Molecular Formula: C 10 H 12 N 5 O 10 P 2 Br (Anion)
Molecular Weight: 504.08 (Anion)
O O
P P
HO O
O O
2 Na
O
Br
O
OH OH
N
N
N
N
N
NH 2
N
2’I-ATP
2’-Iodo-adenosine-5’-triphosphate, Sodium salt
Cat. No. Amount (Units) Price (€)
NU-101S 30 75,--
NU-101L 150 300,--
Molecular Formula: C 10 H 12 N 5 O 12 P 3 I (Anion)
Molecular Weight: 614.05 (Anion)
O
O O
P P P
HO O O O
O O O
3 Na
O
OH I
N
N
NH 2
Selected references:
Gruen et al. (1999) 2’-Halo-ATP and -GTP analogues: Rational
phasing tools for protein crystallography. Protein Sci. 8:2524.
Gruen et al. (1999) Synthesis of 2’-iodo- and 2’-bromo-ATP and
GTP analogues as potential phasing tools for X-ray crystallography.
Nucleos. Nucleot. 18 (1):137.
Naber et al. (1995) A novel adenosine-triphosphate analog with
a heavy-atom to target the nucleotide-binding site of proteins.
Protein Sci. 4:1824.
N
N