JCGGDB TOP Glycan Syntheses

Reaction

JCGG ID
JCGG-RAC0001211
Submitter
The Noguchi Institute
Reaction ID
R-0000-001217
Regist Date
2012/06/21 16:45:28
REACTANT
MOLECULE ID
JCGG-COM0001279 (Reaction Tree)
Mol
0.455 mmol
MOLECULE ID
JCGG-COM0001311 (Reaction Tree)
Mol
0.044 mmol
MOLECULE ID
JCGG-COM0001277
Reactant Type
(BrC6H4)3NSbCl6
Mol
0.5 mmol (total)
PRODUCT
MOLECULE ID
JCGG-COM0001312 (Reaction Tree)
Yield
19%
REACTION DETAIL
Reaction Time
40 minutes, 20 hours
Reaction Temp
10 degree C, room temp
Solvent
dry MeCN, dry MeCN
Comment
1) 21+(BrC6H4)3NSbCl6, 7, MS 3A, 2) the second addition of (BrC6H4)3NSbCl6
MS 3A was included in the solvent.
The reactants were mixed at 10 degree in Celsius, and allowed to warm slowly to room temperature within the reaction time. (second phase)
Before the reaction, 21 and 7 were prepared independently and stirred with MS 3A in MeCN for 1 hour at room temperature.
7 was added dropwise.
COMMENT
Keywords: prostate specific antigen, PSA, N-linked glycan, peptide backbone, antibody, cancer, amino acid, keyhole limpet hemocyanin, KLH
There are two phases in this reaction.
ATTENTION: MeOTf appearing in Scheme 10 is not mentioned in the written method.
ATTENTION: DTBP appearing in Scheme 10 is not mentioned in the written method.
ATTENTION: For solvent, dry MeCN is mentioned in the written method, whereas CH2Cl2 is mentioned in Scheme 10.
REFERENCE
Reference Id
REF-0000-000061
Issn
Electronic
Doi
10.1021/ja8028137
PubMed ID
18798614
Journal Name
Journal of the American Chemical Society. (2008) 130 (41): 13598-607.
Article Title
Toward a prostate specific antigen-based prostate cancer diagnostic assay: preparation of keyhole limpet hemocyanin-conjugated normal and transformed prostate specific antigen fragments.
Author
Vadim Y, Dudkin; Justin S, Miller; Anna S, Dudkina; Christophe, Antczak; David A, Scheinberg; Samuel J, Danishefsky
Affiliation
Laboratory for Bioorganic Chemistry, Sloan-Kettering Institute for Cancer Research, 1275 York Avenue, New York, New York 10065, USA.
Reference Id
REF-0000-000062
Source
J. AM. CHEM. SOC. 2008, 130, 13598-13607
Doi
10.1021/ja8028137

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