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I22404

Sigma-Aldrich

2′,3′-O-Isopropylideneadenosine

98%

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About This Item

Empirical Formula (Hill Notation):
C13H17N5O4
CAS Number:
362-75-4
Molecular Weight:
307.31
Beilstein:
43435
EC Number:
206-650-3
MDL number:
MFCD00005756
UNSPSC Code:
12352204
PubChem Substance ID:
24895967
NACRES:
NA.22

Assay

98%

optical activity

[α]20/D −98.5°, c = 1 in dioxane

mp

221-222 °C (lit.)

SMILES string

CC1(C)O[C@@H]2[C@@H](CO)O[C@H]([C@@H]2O1)n3cnc4c(N)ncnc34

InChI

1S/C13H17N5O4/c1-13(2)21-8-6(3-19)20-12(9(8)22-13)18-5-17-7-10(14)15-4-16-11(7)18/h4-6,8-9,12,19H,3H2,1-2H3,(H2,14,15,16)/t6-,8-,9-,12-/m1/s1

InChI key

LCCLUOXEZAHUNS-WOUKDFQISA-N

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Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Lindsay R Comstock et al.
The Journal of organic chemistry, 69(4), 1425-1428 (2004-02-14)
8-Azido-5'-aziridino-5'-deoxyadenosine (6), a novel cofactor mimic, was synthesized in nine steps from commercially available 2',3'-isopropylideneadenosine in approximately 4% overall yield. Crucial to this success was a very unorthodox phthalimide cleavage procedure, C8 azidation prior to aziridination and late stage alkylation
M Brignoni et al.
Journal of cell science, 108 ( Pt 5), 1931-1943 (1995-05-01)
Madin-Darby canine kidney and other epithelial cell lines (e.g. Caco-2, MCF-10A and MCF-7) develop intracellular vacuoles composed of apical membrane displaying microvilli (VACs) when impaired from forming normal cell-to-cell contacts. In a previous publication, we showed that VACs are rapidly
I D Golovatskiĭ et al.
Ukrainskii biokhimicheskii zhurnal (1978), 61(2), 64-69 (1989-03-01)
Transformation and uptake of [8-14C]-adenosine and its synthetic analog 2',3'-O-isopropylideneadenosine was studied in Zajdel hepatoma cells and their homogenates. Uptake and deamination of adenosine and 2',3'-O-isopropylideneadenosine by Zajdel hepatoma cells proceed differently. A small part of adenosine is phosphorylated and
Pierangela Ciuffreda et al.
Nucleosides, nucleotides & nucleic acids, 26(10-12), 1311-1313 (2007-12-11)
2 ',3 '-Isopropylidene group can be used as a molecular scaffold for the introduction of modifications at 5 ' and 1 ' positions of adenosine and these modified nucleosides are used to evaluate the biocatalytic activity of adenosine and adenylate
I D Golovatskiĭ et al.
Ukrainskii biokhimicheskii zhurnal (1978), 58(3), 37-40 (1986-05-01)
Transformation of synthesized 2',3'-O-isopropylidene adenosine was studied in comparison with adenosine in rat liver homogenates. It is stated that 2',3'-O-isopropylidene adenosine is subjected to deamination similar to adenosine but less intensively. Due to deamination 2',3'-O-isopropylidene inosine is formed from 2',3'-O-isopropylidene
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