Literature DB >> 17425309

Hierarchical assembly of model cell surfaces: synthesis of mucin mimetic polymers and their display on supported bilayers.

David Rabuka1, Raghuveer Parthasarathy, Goo Soo Lee, Xing Chen, Jay T Groves, Carolyn R Bertozzi.   

Abstract

Molecular level analysis of cell-surface phenomena could benefit from model systems comprising structurally defined components. Here we present the first step toward bottom-up assembly of model cell surfaces-the synthesis of mucin mimetics and their incorporation into artificial membranes. Natural mucins are densely glycosylated O-linked glycoproteins that serve numerous functions on cell surfaces. Their large size and extensive glycosylation makes the synthesis of these biopolymers impractical. We designed synthetically tractable glycosylated polymers that possess rodlike extended conformations similar to natural mucins. The glycosylated polymers were end-functionalized with lipid groups and embedded into supported lipid bilayers where they interact with protein receptors in a structure-dependent manner. Furthermore, their dynamic behavior in synthetic membranes mirrored that of natural biomolecules. This system provides a unique framework with which to study the behavior of mucin-like macromolecules in a controlled, cell surface-mimetic environment.

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Year:  2007        PMID: 17425309      PMCID: PMC2535821          DOI: 10.1021/ja067819i

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  24 in total

Review 1.  Molecular transport and organization in supported lipid membranes.

Authors:  S G Boxer
Journal:  Curr Opin Chem Biol       Date:  2000-12       Impact factor: 8.822

2.  Synthesis of oxime-linked mucin mimics containing the tumor-related T(N) and sialyl T(N) antigens.

Authors:  L A Marcaurelle; Y Shin; S Goon; C R Bertozzi
Journal:  Org Lett       Date:  2001-11-15       Impact factor: 6.005

3.  Modular assembly of glycoproteins: towards the synthesis of GlyCAM-1 by using expressed protein ligation.

Authors:  Derek Macmillan; Carolyn R Bertozzi
Journal:  Angew Chem Int Ed Engl       Date:  2004-03-05       Impact factor: 15.336

4.  Biomimetic engineering of carbon nanotubes by using cell surface mucin mimics.

Authors:  Xing Chen; Goo Soo Lee; A Zettl; Carolyn R Bertozzi
Journal:  Angew Chem Int Ed Engl       Date:  2004-11-19       Impact factor: 15.336

Review 5.  Chemoselective ligation reactions with proteins, oligosaccharides and cells.

Authors:  G A Lemieux; C R Bertozzi
Journal:  Trends Biotechnol       Date:  1998-12       Impact factor: 19.536

Review 6.  Mammalian GPI proteins: sorting, membrane residence and functions.

Authors:  O Nosjean; A Briolay; B Roux
Journal:  Biochim Biophys Acta       Date:  1997-09-08

7.  Interfacing carbon nanotubes with living cells.

Authors:  Xing Chen; Un Chong Tam; Jennifer L Czlapinski; Goo Soo Lee; David Rabuka; Alex Zettl; Carolyn R Bertozzi
Journal:  J Am Chem Soc       Date:  2006-05-17       Impact factor: 15.419

Review 8.  Lectin receptors as lymphocyte surface markers.

Authors:  N Sharon
Journal:  Adv Immunol       Date:  1983       Impact factor: 3.543

9.  Formation of solid-supported lipid bilayers: an integrated view.

Authors:  Ralf P Richter; Rémi Bérat; Alain R Brisson
Journal:  Langmuir       Date:  2006-04-11       Impact factor: 3.882

Review 10.  The sweet and sour of cancer: glycans as novel therapeutic targets.

Authors:  Mark M Fuster; Jeffrey D Esko
Journal:  Nat Rev Cancer       Date:  2005-07       Impact factor: 60.716

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  13 in total

1.  Scalable synthesis of Fmoc-protected GalNAc-threonine amino acid and T(N) antigen via nickel catalysis.

Authors:  Fei Yu; Matthew S McConnell; Hien M Nguyen
Journal:  Org Lett       Date:  2015-04-08       Impact factor: 6.005

2.  Utilization of bench-stable and readily available nickel(II) triflate for access to 1,2-cis-2-aminoglycosides.

Authors:  Eric T Sletten; Sai Kumar Ramadugu; Hien M Nguyen
Journal:  Carbohydr Res       Date:  2016-10-24       Impact factor: 2.104

3.  The carbohydrate-binding domain on galectin-1 is more extensive for a complex glycan than for simple saccharides: implications for galectin-glycan interactions at the cell surface.

Authors:  Michelle C Miller; Irina V Nesmelova; David Platt; Anatole Klyosov; Kevin H Mayo
Journal:  Biochem J       Date:  2009-06-26       Impact factor: 3.857

4.  The alpha-galactomannan Davanat binds galectin-1 at a site different from the conventional galectin carbohydrate binding domain.

Authors:  Michelle C Miller; Anatole Klyosov; Kevin H Mayo
Journal:  Glycobiology       Date:  2009-06-18       Impact factor: 4.313

5.  Biocompatible carbon nanotubes generated by functionalization with glycodendrimers.

Authors:  Peng Wu; Xing Chen; Nancy Hu; Un Chong Tam; Ola Blixt; Alex Zettl; Carolyn R Bertozzi
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

6.  Glycocalyx crowding with mucin mimetics strengthens binding of soluble and virus-associated lectins to host cell glycan receptors.

Authors:  Daniel J Honigfort; Meghan O Altman; Pascal Gagneux; Kamil Godula
Journal:  Proc Natl Acad Sci U S A       Date:  2021-10-05       Impact factor: 11.205

7.  Control of the molecular orientation of membrane-anchored biomimetic glycopolymers.

Authors:  Kamil Godula; Marissa L Umbel; David Rabuka; Zsofia Botyanszki; Carolyn R Bertozzi; Raghuveer Parthasarathy
Journal:  J Am Chem Soc       Date:  2009-07-29       Impact factor: 15.419

8.  Noncovalent cell surface engineering: incorporation of bioactive synthetic glycopolymers into cellular membranes.

Authors:  David Rabuka; Martin B Forstner; Jay T Groves; Carolyn R Bertozzi
Journal:  J Am Chem Soc       Date:  2008-04-11       Impact factor: 15.419

9.  Synthesis and microcontact printing of dual end-functionalized mucin-like glycopolymers for microarray applications.

Authors:  Kamil Godula; David Rabuka; Ki Tae Nam; Carolyn R Bertozzi
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

10.  Chemical approaches to perturb, profile, and perceive glycans.

Authors:  Nicholas J Agard; Carolyn R Bertozzi
Journal:  Acc Chem Res       Date:  2009-06-16       Impact factor: 22.384

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