JCGGDB TOP Glycan Syntheses

Reaction

JCGG ID
JCGG-RAC0000521
Submitter
The Noguchi Institute
Reaction ID
R-0000-000522
Regist Date
2012/06/21 16:10:39
REACTANT
MOLECULE ID
JCGG-COM0000502 (Reaction Tree)
Reactant Type
Novel galactosaminyl donor
Mol
93 micro mole
MOLECULE ID
JCGG-COM0000503 (Reaction Tree)
Reactant Type
sialyl-alpha-(2,3)-galactosyl acceptor
Mol
46 micro mole
MOLECULE ID
JCGG-COM0000129
Reactant Type
NIS
Mol
186 micro mole
MOLECULE ID
JCGG-COM0000111
Reactant Type
TfOH
Mol
18 micro mole
PRODUCT
MOLECULE ID
JCGG-COM0000504 (Reaction Tree)
Product Type
alpha
Yield
70%(alpha/beta=1/2.4)
MOLECULE ID
JCGG-COM0000505 (Reaction Tree)
Product Type
beta
Yield
70%(alpha/beta=1/2.4)
REACTION DETAIL
Reaction Time
1 hour, 1.5 hours
Reaction Temp
room temp, -50 degree C
Solvent
CH2Cl2
Catalyst
NIS, TfOH
Comment
MS 4A was included in the solvent.
1) 18+19, 2) NIS, TfOH
COMMENT
The alpha/beta ratio was determined by 1H NMR spectra.
There are two phases in this reaction.
REFERENCE
Reference Id
REF-0000-000021
Issn
Electronic
Doi
10.1016/j.carres.2009.06.009
PubMed ID
19560125
Journal Name
Carbohydrate research. (2009) 344 (12): 1453-63.
Article Title
Study on systematizing the synthesis of the a-series ganglioside glycans GT1a, GD1a, and GM1 using the newly developed N-Troc-protected GM3 and GalN intermediates.
Author
Tatsuya, Komori; Akihiro, Imamura; Hiromune, Ando; Hideharu, Ishida; Makoto, Kiso
Affiliation
Department of Applied Bioorganic Chemistry, Faculty of Applied Biological Sciences, Gifu University, 1-1 Yanagido, Gifu-shi, Gifu 501-1193, Japan.
Reference Id
REF-0000-000022
Source
Carbohydrate Research, 344 (2009), 1453-1463
Doi
10.1016/j.carres.2009.06.009

©2008-2013 Research Center for Medical Glycoscience, National Institute of Advanced Industrial Science and Technology (AIST)