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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

Quality Level

100

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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
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
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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