Synthesis of oligosaccharide dendrimers

Barbara Colonna, Valerie D. Harding, Sergey A. Nepogodiev, Francisco Raymo, Neil Spencer, J. Fraser Stoddart

Research output: Contribution to journalArticle

56 Citations (Scopus)

Abstract

Two β-D-glucopyranoside-based dendrimers, one incorporating three tetra- and the other three heptasaccharide wedges attached to a central trisfunctionalized nonsaccharide core component, have been synthesized. Branching at designated saccharide units of the tetra- and of the heptasaccharide wedges arises from (1→2)/ (1→3)/(1→6) and from (1→3)/(1→6) intersaccharide linkages, respectively, with the 1,2-trans configuration at all anomeric centers. Both oligosaccharide wedges were constructed by stepwise glycosylation strategies and have reactive primary amino groups at their focal points located at the termini of spacer arms connected to the reducing glucose residues. Amide bond formation between these amino groups and appropriate core components carrying three carboxylic acid functions afforded two dendrimers incorporating a total of 12 and 21 monosaccharide units when the tetra- and the heptasaccharide wedges were employed, respectively. These nanosized highly branched macromolecules possess molecular diameters of 5-6 nm and molecular weights of 6195 and 10008 Daltons for the 12-mer and 21-mer, respectively. The wedges and dendrimers were characterized and the intersaccharide connectivity elucidated by extensive mono- and bidimensional 1H and 13C NMR spectroscopic investigations. In addition, LSIMS and MAL-DI-TOFMS investigations were also performed and revealed molecular ion peaks generally as H, Na, or K adducts for all oligosaccharides.

Original languageEnglish
Pages (from-to)1244-1254
Number of pages11
JournalChemistry - A European Journal
Volume4
Issue number7
DOIs
StatePublished - Jan 1 1998
Externally publishedYes

Fingerprint

Dendrimers
Oligosaccharides
Glycosylation
Monosaccharides
Carboxylic Acids
Macromolecules
Carboxylic acids
Amides
Glucose
Molecular weight
Nuclear magnetic resonance
Ions

Keywords

  • Carbohydrates
  • Dendrimers
  • Glycosylations
  • Nano-structures
  • Oligosaccharides

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Colonna, B., Harding, V. D., Nepogodiev, S. A., Raymo, F., Spencer, N., & Stoddart, J. F. (1998). Synthesis of oligosaccharide dendrimers. Chemistry - A European Journal, 4(7), 1244-1254. https://doi.org/10.1002/(SICI)1521-3765(19980710)4:7<1244::AID-CHEM1244>3.0.CO;2-8

Synthesis of oligosaccharide dendrimers. / Colonna, Barbara; Harding, Valerie D.; Nepogodiev, Sergey A.; Raymo, Francisco; Spencer, Neil; Stoddart, J. Fraser.

In: Chemistry - A European Journal, Vol. 4, No. 7, 01.01.1998, p. 1244-1254.

Research output: Contribution to journalArticle

Colonna, B, Harding, VD, Nepogodiev, SA, Raymo, F, Spencer, N & Stoddart, JF 1998, 'Synthesis of oligosaccharide dendrimers', Chemistry - A European Journal, vol. 4, no. 7, pp. 1244-1254. https://doi.org/10.1002/(SICI)1521-3765(19980710)4:7<1244::AID-CHEM1244>3.0.CO;2-8
Colonna, Barbara ; Harding, Valerie D. ; Nepogodiev, Sergey A. ; Raymo, Francisco ; Spencer, Neil ; Stoddart, J. Fraser. / Synthesis of oligosaccharide dendrimers. In: Chemistry - A European Journal. 1998 ; Vol. 4, No. 7. pp. 1244-1254.
@article{921080d51224402bb5e4bc38a1ef6f3a,
title = "Synthesis of oligosaccharide dendrimers",
abstract = "Two β-D-glucopyranoside-based dendrimers, one incorporating three tetra- and the other three heptasaccharide wedges attached to a central trisfunctionalized nonsaccharide core component, have been synthesized. Branching at designated saccharide units of the tetra- and of the heptasaccharide wedges arises from (1→2)/ (1→3)/(1→6) and from (1→3)/(1→6) intersaccharide linkages, respectively, with the 1,2-trans configuration at all anomeric centers. Both oligosaccharide wedges were constructed by stepwise glycosylation strategies and have reactive primary amino groups at their focal points located at the termini of spacer arms connected to the reducing glucose residues. Amide bond formation between these amino groups and appropriate core components carrying three carboxylic acid functions afforded two dendrimers incorporating a total of 12 and 21 monosaccharide units when the tetra- and the heptasaccharide wedges were employed, respectively. These nanosized highly branched macromolecules possess molecular diameters of 5-6 nm and molecular weights of 6195 and 10008 Daltons for the 12-mer and 21-mer, respectively. The wedges and dendrimers were characterized and the intersaccharide connectivity elucidated by extensive mono- and bidimensional 1H and 13C NMR spectroscopic investigations. In addition, LSIMS and MAL-DI-TOFMS investigations were also performed and revealed molecular ion peaks generally as H, Na, or K adducts for all oligosaccharides.",
keywords = "Carbohydrates, Dendrimers, Glycosylations, Nano-structures, Oligosaccharides",
author = "Barbara Colonna and Harding, {Valerie D.} and Nepogodiev, {Sergey A.} and Francisco Raymo and Neil Spencer and Stoddart, {J. Fraser}",
year = "1998",
month = "1",
day = "1",
doi = "10.1002/(SICI)1521-3765(19980710)4:7<1244::AID-CHEM1244>3.0.CO;2-8",
language = "English",
volume = "4",
pages = "1244--1254",
journal = "Chemistry - A European Journal",
issn = "0947-6539",
publisher = "Wiley-VCH Verlag",
number = "7",

}

TY - JOUR

T1 - Synthesis of oligosaccharide dendrimers

AU - Colonna, Barbara

AU - Harding, Valerie D.

AU - Nepogodiev, Sergey A.

AU - Raymo, Francisco

AU - Spencer, Neil

AU - Stoddart, J. Fraser

PY - 1998/1/1

Y1 - 1998/1/1

N2 - Two β-D-glucopyranoside-based dendrimers, one incorporating three tetra- and the other three heptasaccharide wedges attached to a central trisfunctionalized nonsaccharide core component, have been synthesized. Branching at designated saccharide units of the tetra- and of the heptasaccharide wedges arises from (1→2)/ (1→3)/(1→6) and from (1→3)/(1→6) intersaccharide linkages, respectively, with the 1,2-trans configuration at all anomeric centers. Both oligosaccharide wedges were constructed by stepwise glycosylation strategies and have reactive primary amino groups at their focal points located at the termini of spacer arms connected to the reducing glucose residues. Amide bond formation between these amino groups and appropriate core components carrying three carboxylic acid functions afforded two dendrimers incorporating a total of 12 and 21 monosaccharide units when the tetra- and the heptasaccharide wedges were employed, respectively. These nanosized highly branched macromolecules possess molecular diameters of 5-6 nm and molecular weights of 6195 and 10008 Daltons for the 12-mer and 21-mer, respectively. The wedges and dendrimers were characterized and the intersaccharide connectivity elucidated by extensive mono- and bidimensional 1H and 13C NMR spectroscopic investigations. In addition, LSIMS and MAL-DI-TOFMS investigations were also performed and revealed molecular ion peaks generally as H, Na, or K adducts for all oligosaccharides.

AB - Two β-D-glucopyranoside-based dendrimers, one incorporating three tetra- and the other three heptasaccharide wedges attached to a central trisfunctionalized nonsaccharide core component, have been synthesized. Branching at designated saccharide units of the tetra- and of the heptasaccharide wedges arises from (1→2)/ (1→3)/(1→6) and from (1→3)/(1→6) intersaccharide linkages, respectively, with the 1,2-trans configuration at all anomeric centers. Both oligosaccharide wedges were constructed by stepwise glycosylation strategies and have reactive primary amino groups at their focal points located at the termini of spacer arms connected to the reducing glucose residues. Amide bond formation between these amino groups and appropriate core components carrying three carboxylic acid functions afforded two dendrimers incorporating a total of 12 and 21 monosaccharide units when the tetra- and the heptasaccharide wedges were employed, respectively. These nanosized highly branched macromolecules possess molecular diameters of 5-6 nm and molecular weights of 6195 and 10008 Daltons for the 12-mer and 21-mer, respectively. The wedges and dendrimers were characterized and the intersaccharide connectivity elucidated by extensive mono- and bidimensional 1H and 13C NMR spectroscopic investigations. In addition, LSIMS and MAL-DI-TOFMS investigations were also performed and revealed molecular ion peaks generally as H, Na, or K adducts for all oligosaccharides.

KW - Carbohydrates

KW - Dendrimers

KW - Glycosylations

KW - Nano-structures

KW - Oligosaccharides

UR - http://www.scopus.com/inward/record.url?scp=0031825396&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0031825396&partnerID=8YFLogxK

U2 - 10.1002/(SICI)1521-3765(19980710)4:7<1244::AID-CHEM1244>3.0.CO;2-8

DO - 10.1002/(SICI)1521-3765(19980710)4:7<1244::AID-CHEM1244>3.0.CO;2-8

M3 - Article

AN - SCOPUS:0031825396

VL - 4

SP - 1244

EP - 1254

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

SN - 0947-6539

IS - 7

ER -