Repository logo

Infoscience

  • English
  • French
Log In
Logo EPFL, École polytechnique fédérale de Lausanne

Infoscience

  • English
  • French
Log In
  1. Home
  2. Academic and Research Output
  3. Journal articles
  4. The C-disaccharide alpha-C(1 -> 3)-mannopyranoside of N-acetylgalactosamine is an inhibitor of glycohydrolases and of human alpha-1,3-fucosyltransferase VI. its epimer alpha-(1 -> 3)-mannopyranoside of N-acetyltalosamine is not
 
research article

The C-disaccharide alpha-C(1 -> 3)-mannopyranoside of N-acetylgalactosamine is an inhibitor of glycohydrolases and of human alpha-1,3-fucosyltransferase VI. its epimer alpha-(1 -> 3)-mannopyranoside of N-acetyltalosamine is not

Pasquarello, C.
•
Picasso, S.
•
Demange, R.  
Show more
2000
The Journal of Organic Chemistry

The radical C-glycosidation of (-)-(1S,4R,5R,6R)-6-endo-chloro-3-methylidene-5-exo-(phenylseleno)-7-oxa bicyclo[2.2.1]heptan-2-one ((-)-4) with 2,3,4,6-tetra-O-acetyl-alpha-D-mannopyranosyl bromide gave (+)-(1S,3R,4R,5R,6R)-6-endo-chloro-5-exo-(phenylseleno)-3-endo-(1',3',4' ,5'-tetra-O-acetyl-2',6'-anhydro-7'-deoxy-D-glycero-D-manno-heptitol-7'- C-yl)-7-oxabicyclo[2.2.1]hept-2-one ((+)-5) that was converted into (+)-(1R,2S,5R,6R)-5-acetamido-3-chloro-2-anhydro-6-(1R,2S,5R,6R)-5-aceta mido-3-chloro-2-hydroxy-6-(1',3',4',5'-tetra-O-acetyl)-2',6'-anhydro-7'- deoxy-D- glycero-D-manno-heptitol-7'-C-yl)cyclohex-3-en-1-yl acetate ((+)-10) and into (+)-(1R,2S,5R,6S)-5-bromo-3-chloro-2-hydroxy-6-(1',3',4',5',-tetra-O-ace tyl-2',6'-anhydro-7'-deoxy-D-glycero-D-manno-heptitol-7'-C-yl)cyclohex-3 -en-1-yl acetate ((+)-19). Ozonolysis of (+)-10 and further transformations provided 2-acetamido-2,3-dideoxy-3-C-(2',6'-anhydro-7'-deoxy-D-glycero-D-manno- heptitol-7'-C-yl)-D-galactose (alpha-C(1-->3)-D-mannopyranoside of N-acetylgalactosamine (alpha-D-Manp-(1-->3)CH2-D-GalNAc): 1). Displacement of the bromide (+)-19 with NaN3 in DMF provided the corresponding azide ((-)-20) following a SN2 mechanism. Ozonolysis of (-)-20 and further transformations led to 2-acetamido-2,3-dideoxy-3-C-(2',6'-anhydro-7'-deoxy-D-glycerol-D-manno-h eptitol-7'-C-yl)-D-talose (alpha-C(1-->3)-D-mannopyranoside of N-acetyl D-talosamine (alpha-D-Manp-(1-->3)CH2-D-TalNAc): 2). The neutral C-disaccharide 1 inhibits several glycosidases (e.g., beta-galactosidase from jack bean with K-i = 7.5 mu M, alpha-L-fucosidase from human placenta with K-i = 28 mu M, beta-glucosidase from Caldocellum saccharolyticum with K-i = 18 mu M) and human alpha-1,3-fucosyltransferase VI (Fuc-TVI) with K-i = 120 mu M whereas it 2-epimer 2 does not. Double reciprocal analysis showed that the inhibition of Fuc-TVI by 1 displays a mixed pattern with respect to both the donor sugar GDP-fucose and the acceptor LacNAc with K-i of 123 and 128 mu M, respectively.

  • Details
  • Metrics
Type
research article
DOI
10.1021/jo991952u
Author(s)
Pasquarello, C.
Picasso, S.
Demange, R.  
Malissard, M.
Berger, E. G.
Vogel, P.  
Date Issued

2000

Published in
The Journal of Organic Chemistry
Volume

65

Issue

14

Start page

4251

End page

4260

Subjects

Fucosyl-transferase genes

•

alpha-l-fucosidase

•

sialyl-lewis-x

•

stereoselective synthesis

•

7-oxabicyclo<2.2.1>hept-2-ene derivatives

•

human alpha-1

•

3-fucosyl-transferase-v

•

conformational-analysis

•

preferred conformation

•

leukocyte trafficking

•

wittig olefination

Note

Univ Lausanne, BCH, Chim Sect, CH-1015 Lausanne, Switzerland. Univ Zurich, Inst Physiol, CH-8057 Zurich, Switzerland.

Editorial or Peer reviewed

REVIEWED

Written at

EPFL

EPFL units
LGSA  
Available on Infoscience
November 9, 2005
Use this identifier to reference this record
https://infoscience.epfl.ch/handle/20.500.14299/219768
Logo EPFL, École polytechnique fédérale de Lausanne
  • Contact
  • infoscience@epfl.ch

  • Follow us on Facebook
  • Follow us on Instagram
  • Follow us on LinkedIn
  • Follow us on X
  • Follow us on Youtube
AccessibilityLegal noticePrivacy policyCookie settingsEnd User AgreementGet helpFeedback

Infoscience is a service managed and provided by the Library and IT Services of EPFL. © EPFL, tous droits réservés