Synthesis of the saccharide moiety of galactosylgloboside (SSEA-3) and its conjugation to bovine serum albumin and sepharose
(1995) In Carbohydrate Research 272(1). p.9-16- Abstract
The pentasaccharide glycoside corresponding to galactosylgloboside (SSEA-3), β-d-Gal p-(1 → 3)-β-d-Gal pNAc-(1 → 3)-α-d-Gal p-(1 → 4)-β-d-Gal p-(1 → 4)-β-d-Glc p-1-OCH2CH2Si-(CH3)3 (4), was synthesized via glycosylation (87%) of 2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-4-O-[2,3,6-tri-O-benzyl-4-O-(2,4,6-tri-O-benzyl-α-d-galactopyranosyl)-β-d- galactopyranosyl]-β-d-glucopyranoside (2) with the glycosyl donor methyl 4,6-di-O-acetyl-2-deoxy-2-phthalimido-3-O-(2,3,4,6-tetra-O-acetyl-β-d-galactopyranosyl)-1-thio-β-d -galactopyranoside (1), followed by removal of protecting groups. Compound 4 was transformed into the spacer glycoside β-d-Gal p-(1 → 3)-β-d-Gal pNAc-(1 → 3)-α-d-Gal p-(1 → 4)-β-d-Gal... (More)
The pentasaccharide glycoside corresponding to galactosylgloboside (SSEA-3), β-d-Gal p-(1 → 3)-β-d-Gal pNAc-(1 → 3)-α-d-Gal p-(1 → 4)-β-d-Gal p-(1 → 4)-β-d-Glc p-1-OCH2CH2Si-(CH3)3 (4), was synthesized via glycosylation (87%) of 2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-4-O-[2,3,6-tri-O-benzyl-4-O-(2,4,6-tri-O-benzyl-α-d-galactopyranosyl)-β-d- galactopyranosyl]-β-d-glucopyranoside (2) with the glycosyl donor methyl 4,6-di-O-acetyl-2-deoxy-2-phthalimido-3-O-(2,3,4,6-tetra-O-acetyl-β-d-galactopyranosyl)-1-thio-β-d -galactopyranoside (1), followed by removal of protecting groups. Compound 4 was transformed into the spacer glycoside β-d-Gal p-(1 → 3)-β-d-Gal pNAc-(1 → 3)-α-d-Gal p-(1 → 4)-β-d-Gal p-(1 → 4)-β-d-Glcp-1-SCH2CH2COOH (10), which was coupled to bovine serum albumin (BSA), and Sepharose beads, to give the corresponding neoglycoprotein (11, 6 mol of saccharide/mol of BSA) and glycosylated Sepharose (12, 2.7 μmol of saccharide/mL of sedimented beads), respectively. An improved synthesis of a protected globotetraoside β-d-Gal pNAc-(1 → 3)-α-d-Gal p-(1 → 4)-β-d-Gal p-(1 → 4)-β-d-Glc p-1-OCH2CH2SiMe3 is also reported.
(Less)
- author
- Nilsson, Ulf LU and Magnusson, Göran LU
- organization
- publishing date
- 1995-07-21
- type
- Contribution to journal
- publication status
- published
- subject
- keywords
- 2-(Trimethylsilyl)ethyl glycoside, BSA-conjugate, Galactosylgloboside, Sepharose-conjugate, Thioglycoside donor
- in
- Carbohydrate Research
- volume
- 272
- issue
- 1
- pages
- 8 pages
- publisher
- Elsevier
- external identifiers
-
- scopus:0028991218
- pmid:7648586
- ISSN
- 0008-6215
- DOI
- 10.1016/0008-6215(95)00044-T
- language
- English
- LU publication?
- yes
- id
- b0923587-06ae-434b-897a-47dbb4104756
- date added to LUP
- 2023-02-07 09:47:58
- date last changed
- 2023-12-20 09:00:48
@article{b0923587-06ae-434b-897a-47dbb4104756, abstract = {{<p>The pentasaccharide glycoside corresponding to galactosylgloboside (SSEA-3), β-d-Gal p-(1 → 3)-β-d-Gal pNAc-(1 → 3)-α-d-Gal p-(1 → 4)-β-d-Gal p-(1 → 4)-β-d-Glc p-1-OCH<sub>2</sub>CH<sub>2</sub>Si-(CH<sub>3</sub>)<sub>3</sub> (4), was synthesized via glycosylation (87%) of 2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-4-O-[2,3,6-tri-O-benzyl-4-O-(2,4,6-tri-O-benzyl-α-d-galactopyranosyl)-β-d- galactopyranosyl]-β-d-glucopyranoside (2) with the glycosyl donor methyl 4,6-di-O-acetyl-2-deoxy-2-phthalimido-3-O-(2,3,4,6-tetra-O-acetyl-β-d-galactopyranosyl)-1-thio-β-d -galactopyranoside (1), followed by removal of protecting groups. Compound 4 was transformed into the spacer glycoside β-d-Gal p-(1 → 3)-β-d-Gal pNAc-(1 → 3)-α-d-Gal p-(1 → 4)-β-d-Gal p-(1 → 4)-β-d-Glcp-1-SCH<sub>2</sub>CH<sub>2</sub>COOH (10), which was coupled to bovine serum albumin (BSA), and Sepharose beads, to give the corresponding neoglycoprotein (11, 6 mol of saccharide/mol of BSA) and glycosylated Sepharose (12, 2.7 μmol of saccharide/mL of sedimented beads), respectively. An improved synthesis of a protected globotetraoside β-d-Gal pNAc-(1 → 3)-α-d-Gal p-(1 → 4)-β-d-Gal p-(1 → 4)-β-d-Glc p-1-OCH<sub>2</sub>CH<sub>2</sub>SiMe<sub>3</sub> is also reported.</p>}}, author = {{Nilsson, Ulf and Magnusson, Göran}}, issn = {{0008-6215}}, keywords = {{2-(Trimethylsilyl)ethyl glycoside; BSA-conjugate; Galactosylgloboside; Sepharose-conjugate; Thioglycoside donor}}, language = {{eng}}, month = {{07}}, number = {{1}}, pages = {{9--16}}, publisher = {{Elsevier}}, series = {{Carbohydrate Research}}, title = {{Synthesis of the saccharide moiety of galactosylgloboside (SSEA-3) and its conjugation to bovine serum albumin and sepharose}}, url = {{http://dx.doi.org/10.1016/0008-6215(95)00044-T}}, doi = {{10.1016/0008-6215(95)00044-T}}, volume = {{272}}, year = {{1995}}, }