liu.seSearch for publications in DiVA
Endre søk
RefereraExporteraLink to record
Permanent link

Direct link
Referera
Referensformat
  • apa
  • ieee
  • modern-language-association-8th-edition
  • vancouver
  • oxford
  • Annet format
Fler format
Språk
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Annet språk
Fler språk
Utmatningsformat
  • html
  • text
  • asciidoc
  • rtf
Synthesis of tri-, penta-, and hepta-saccharides, functionalized with Orthogonally N-Protected Amino residues at the reducing and non-reducing ends
Linköpings universitet, Institutionen för fysik, kemi och biologi, Organisk Kemi. Linköpings universitet, Tekniska högskolan.
Linköpings universitet, Institutionen för fysik, kemi och biologi, Organisk Kemi. Linköpings universitet, Tekniska högskolan.
Linköpings universitet, Institutionen för fysik, kemi och biologi, Organisk Kemi. Linköpings universitet, Tekniska högskolan.
2012 (engelsk)Inngår i: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 68, nr 33, s. 6712-6720Artikkel i tidsskrift (Fagfellevurdert) Published
Abstract [en]

The synthesis of four bifunctionalized orthogonally N-protected oligosaccharides derived from lactose and mannose, intended as cross-linking derivatives, is described. The amino sugar at the non-reducing end is derivatized with an N-Boc-protected glycine moiety, and further connected to either a mannose (1→6) disaccharide or (1→3) lactose units (one, two or three) resulting in tri-, penta-, or heptasaccharides. All of the synthesized oligosaccharides have an Nbenzyloxycarbonyl-aminoethyl residue at the reducing end. The fully orthogonal N-Boc/N-Cbz protection group pattern enables further conjugation/derivatization and results in a hydrophilic cross-linking molecule. It was found that the order of the final synthetic steps were crucial to avoid acyl migration. A suitable amide coupling protocol has been applied to introduce the NBoc-protected glycine moiety in alcoholic solvent. The synthesized oligosaccharides will provide a model system to investigate the influence of length, structure and flexibility. The function of the cross-linked substituents thereby provide valuable insights into the role as a spacer molecule.

sted, utgiver, år, opplag, sider
2012. Vol. 68, nr 33, s. 6712-6720
Emneord [en]
Glycosylation, glycosidation, oligosaccharide synthesis, spacer molecules, orthogonally protected, carbohydrates, bifunctionalized
HSV kategori
Identifikatorer
URN: urn:nbn:se:liu:diva-76730DOI: 10.1016/j.tet.2012.05.118ISI: 000306618400009OAI: oai:DiVA.org:liu-76730DiVA, id: diva2:516487
Tilgjengelig fra: 2012-04-18 Laget: 2012-04-18 Sist oppdatert: 2017-12-07bibliografisk kontrollert
Inngår i avhandling
1. Synthesis of Orthogonally Functionalized Oligosaccharides for Self-assembled Monolayers and as Multimodal Tools in Chemical Biology
Åpne denne publikasjonen i ny fane eller vindu >>Synthesis of Orthogonally Functionalized Oligosaccharides for Self-assembled Monolayers and as Multimodal Tools in Chemical Biology
2012 (engelsk)Doktoravhandling, med artikler (Annet vitenskapelig)
Abstract [en]

This thesis covers different topics in the field of synthetic organic chemistry combined with the field of surface science and glycobiology.

First, the text presents a series of orthogonally protected oligosaccharides (tri-, penta-, and heptasaccharides) of varying length and structures, which are synthesized with the aim of developing novel heterobifunctional biocompatible cross-linkers. Successful conjugation with different chemical handles is also described and used to illustrate the potential implementation of defined carbohydrate based compounds have potential use in biosensing applications. The results of incubation experiments using living cells indicate that the linker is incorporated into cell surfaces and enriched in microdomains.

Second, synthesis of various saccharide-terminated alkane thiols immobilized on gold surfaces is reported. The protein adsorption and antifouling characteristics of these surfaces were investigated using model proteins and the common fouling organisms, Ulva linza and Balanus amphitrite.

Further, oligo(lactose)-based thiols (di-, tetra-, and hexasaccharides) were synthesized and immobilized on gold nanoparticles to investigate how well these rigid, rod-like oligosaccharides can stabilize such nanoparticles for future use in constructing hybrid nanoparticles.

Finally, the thesis describes synthesis of a systematic series of oligo(ethylene) glycols possessing either hydrogen- or methyl-terminated groups. Investigation of the fundamental characteristics of self-assembled monolayers, will give important insights into the design of protein repellant surfaces.

sted, utgiver, år, opplag, sider
Linköping: Linköping University Electronic Press, 2012. s. 65
Serie
Linköping Studies in Science and Technology. Dissertations, ISSN 0345-7524 ; 1442
Emneord
Oligosaccharide synthesis, glycosylation, thioglycosides, orthogonally protected, oligo(lactosides), spacer molecule, heterobifunctional, surface plasmon resonance, lipid anchor, self-assembled monolayers, glyconanoparticles
HSV kategori
Identifikatorer
urn:nbn:se:liu:diva-76733 (URN)978-91-7519-906-1 (ISBN)
Disputas
2012-05-11, Planck, Fysikhuset, Campus Valla, Linköpings universitet, Linköping, 10:15 (engelsk)
Opponent
Veileder
Tilgjengelig fra: 2012-04-18 Laget: 2012-04-18 Sist oppdatert: 2019-12-08bibliografisk kontrollert

Open Access i DiVA

fulltext(716 kB)622 nedlastinger
Filinformasjon
Fil FULLTEXT01.pdfFilstørrelse 716 kBChecksum SHA-512
855359cb02083b5eb3ff7e18155336d352c36a51facb5a96d7756be013e48b42eed9c755ccbe23b1ea61080589deb817a73da44157328a497a7e90e16926107f
Type fulltextMimetype application/pdf

Andre lenker

Forlagets fulltekst

Personposter BETA

Fyrner, TimmySvensson, Stefan C.T.Konradsson, Peter

Søk i DiVA

Av forfatter/redaktør
Fyrner, TimmySvensson, Stefan C.T.Konradsson, Peter
Av organisasjonen
I samme tidsskrift
Tetrahedron

Søk utenfor DiVA

GoogleGoogle Scholar
Totalt: 622 nedlastinger
Antall nedlastinger er summen av alle nedlastinger av alle fulltekster. Det kan for eksempel være tidligere versjoner som er ikke lenger tilgjengelige

doi
urn-nbn

Altmetric

doi
urn-nbn
Totalt: 470 treff
RefereraExporteraLink to record
Permanent link

Direct link
Referera
Referensformat
  • apa
  • ieee
  • modern-language-association-8th-edition
  • vancouver
  • oxford
  • Annet format
Fler format
Språk
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Annet språk
Fler språk
Utmatningsformat
  • html
  • text
  • asciidoc
  • rtf