Chemoenzymatic synthesis of Galα1-3Gal, Galα1-3Galβ1-4GlcNAc and their PEG-conjugates.
✍ Scribed by Ichiro Matsuo; Hiroshi Fujimoto; Megumi Isomura; Katsumi Ajisaka
- Publisher
- Elsevier Science
- Year
- 1997
- Tongue
- English
- Weight
- 196 KB
- Volume
- 7
- Category
- Article
- ISSN
- 0960-894X
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✦ Synopsis
Galc~l-3Gal-pNP was prepared enzymatically from Gal-pNP using et-galactosidase from coffee beans. PEG was attached after the reduction of nitro group into amino group to give Galal-3GaI-PEG conjugate. After removing the pNP group in Galctl.-3Gal-pNP, the obtained disaccharide was used for the synthesis of Galct l-3Gal[31-4GlcNAc and corresponding trisaccharide-PEG conjugate.
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The title trisaccharide-serine conjugate 1 constituting the linkage region between glycoaminoglycaa and I~otein in proteoglycan, was synthesized via a Ixisacchm~k p-nitrophenyl (PNP) glycoside prepared by stepwise enzymatic transglycosidation to XyI-PNP with a ~-D-galactosidase. In the second tnmsgl
## Abstract A versatile synthesis of the Gal‐α‐(1→3)‐Gal‐β‐(1→4)‐GlcNAc epitope coupled to an alkyl spacer molecule could be developed. The important building block 3′‐allyl‐D‐lactal 6 was prepared in high yield by the action of dibutyltin oxide and allyl bromide on D‐lactal and converted in severa