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I4377

Sigma-Aldrich

2′,3′-O-Isopropylideneguanosine

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Empirical Formula (Hill Notation):
C13H17N5O5
CAS Number:
362-76-5
Molecular Weight:
323.30
EC Number:
206-651-9
MDL number:
MFCD00057081
UNSPSC Code:
41106305
PubChem Substance ID:
24896054
NACRES:
NA.51

biological source

synthetic (organic)

Quality Level

100

Assay

≥98% (HPLC)

form

powder

storage temp.

−20°C

SMILES string

CC1(C)O[C@@H]2[C@@H](CO)O[C@H]([C@@H]2O1)n3cnc4C(=O)NC(N)=Nc34

InChI

1S/C13H17N5O5/c1-13(2)22-7-5(3-19)21-11(8(7)23-13)18-4-15-6-9(18)16-12(14)17-10(6)20/h4-5,7-8,11,19H,3H2,1-2H3,(H3,14,16,17,20)/t5-,7-,8-,11-/m1/s1

InChI key

XKPDAYWPKILAMO-IOSLPCCCSA-N

Application

2′,3′-O-Isopropylideneguanosine derivatives may be used as cap analogs.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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G N Bennett et al.
Biochemistry, 14(14), 3152-3158 (1975-07-15)
A number of synthetic methods for the preparation of the 2-O-(alpha-methoxyethyl) derivatives of the 5-diphosphates of adenosine, cytidine, guanosine, and uridine have been studied in order to provide nucleotide substrates that can be applied to the synthesis of specific oligoribonucleotides
H Kasai et al.
Environmental health perspectives, 67, 111-116 (1986-08-01)
Heated glucose is mutagenic to Salmonella typhimurium TA 100 in the absence of S-9 mix. For identifying unknown mutagens in heated glucose (dry solid, 200 degrees C, 20 min), reaction with isopropylideneguanosine (IPG) was followed by isolation and characterization of
H Kasai et al.
IARC scientific publications, 70(70), 413-418 (1986-01-01)
Mutagens present in crude samples such as heated glucose can be detected or identified by means of the adducts formed upon reaction with a fluorescent guanosine derivative (FG) or isopropylideneguanosine (IPG). After the reaction of IPG with heated glucose, two
Anilkumar R Kore et al.
Bioorganic & medicinal chemistry letters, 18(17), 4828-4832 (2008-08-08)
The synthesis and biological evaluation of a new cap analog, which is modified at the C2' and C3' positions of N(7)-methylguanosine is reported. The new cap analog, P(1)-2',3'-isopropylidene, 7-methylguanosine-5'P(3)-guanosine-5'triphosphate was assayed with respect to its effects on efficiency of incorporation

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