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Metabolic installation of thiols into sialic acid modulates adhesion and stem cell biology

Metabolic 'oligosaccharide engineering' methods based on N-acetyl-D-mannosamine (ManNAc) analogs allow the glycocalyx of living cells to be remodeled. Herein we report the analog Ac5ManNTGc (1) that enables thiols to be expressed in surface sialic acids. By locating this versatile functional group o... Full description

Journal Title: Nature chemical biology 2006-03, Vol.2 (3), p.149-152
Main Author: Yarema, Kevin J
Other Authors: Sampathkumar, Srinivasa-Gopalan , Li, Adrienne V , Jones, Mark B , Sun, Zhonghui
Format: Electronic Article Electronic Article
Language: English
Subjects:
Quelle: Alma/SFX Local Collection
Publisher: United States: Nature Publishing Group
ID: ISSN: 1552-4450
Link: https://www.ncbi.nlm.nih.gov/pubmed/16474386
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title: Metabolic installation of thiols into sialic acid modulates adhesion and stem cell biology
format: Article
creator:
  • Yarema, Kevin J
  • Sampathkumar, Srinivasa-Gopalan
  • Li, Adrienne V
  • Jones, Mark B
  • Sun, Zhonghui
subjects:
  • Acids
  • beta Catenin - metabolism
  • Biotechnology
  • Cell adhesion & migration
  • Cell Adhesion - drug effects
  • Cell Adhesion - physiology
  • Cell Differentiation - physiology
  • Cell Membrane - physiology
  • Cellular biology
  • Gold - chemistry
  • Hexosamines - chemistry
  • Hexosamines - metabolism
  • Humans
  • Jurkat Cells
  • Ligands
  • Metabolism
  • Molecular Conformation
  • N-Acetylneuraminic Acid - biosynthesis
  • N-Acetylneuraminic Acid - chemistry
  • Stem cells
  • Stem Cells - chemistry
  • Stem Cells - physiology
  • Sugar
  • Sulfhydryl Compounds - chemistry
  • Sulfhydryl Compounds - metabolism
  • Sulfhydryl Compounds - pharmacology
  • Surface Properties
  • Up-Regulation
ispartof: Nature chemical biology, 2006-03, Vol.2 (3), p.149-152
description: Metabolic 'oligosaccharide engineering' methods based on N-acetyl-D-mannosamine (ManNAc) analogs allow the glycocalyx of living cells to be remodeled. Herein we report the analog Ac5ManNTGc (1) that enables thiols to be expressed in surface sialic acids. By locating this versatile functional group on the outer periphery of normally nonadhesive human Jurkat cells, we obtained spontaneous cell-cell clustering and attachment to complementary maleimide-derivatized substrates. When analyzed in human embryoid body-derived (hEBD) stem cells, Ac5ManNTGc induced β-catenin expression and altered cell morphology, consistent with neuronal differentiation. Notably, these effects were modulated by the growth substrate of the cells, with a stronger response observed on a gold surface than on glass. Together, these results establish sugar analogs as small-molecule tools for tissue engineering by providing a method for attaching cells to scaffolds via their surface carbohydrates as well as offering a means to influence stem cell fates.
language: eng
source: Alma/SFX Local Collection
identifier: ISSN: 1552-4450
fulltext: fulltext
issn:
  • 1552-4450
  • 1552-4469
url: Link


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descriptionMetabolic 'oligosaccharide engineering' methods based on N-acetyl-D-mannosamine (ManNAc) analogs allow the glycocalyx of living cells to be remodeled. Herein we report the analog Ac5ManNTGc (1) that enables thiols to be expressed in surface sialic acids. By locating this versatile functional group on the outer periphery of normally nonadhesive human Jurkat cells, we obtained spontaneous cell-cell clustering and attachment to complementary maleimide-derivatized substrates. When analyzed in human embryoid body-derived (hEBD) stem cells, Ac5ManNTGc induced β-catenin expression and altered cell morphology, consistent with neuronal differentiation. Notably, these effects were modulated by the growth substrate of the cells, with a stronger response observed on a gold surface than on glass. Together, these results establish sugar analogs as small-molecule tools for tissue engineering by providing a method for attaching cells to scaffolds via their surface carbohydrates as well as offering a means to influence stem cell fates.
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subjectAcids ; beta Catenin - metabolism ; Biotechnology ; Cell adhesion & migration ; Cell Adhesion - drug effects ; Cell Adhesion - physiology ; Cell Differentiation - physiology ; Cell Membrane - physiology ; Cellular biology ; Gold - chemistry ; Hexosamines - chemistry ; Hexosamines - metabolism ; Humans ; Jurkat Cells ; Ligands ; Metabolism ; Molecular Conformation ; N-Acetylneuraminic Acid - biosynthesis ; N-Acetylneuraminic Acid - chemistry ; Stem cells ; Stem Cells - chemistry ; Stem Cells - physiology ; Sugar ; Sulfhydryl Compounds - chemistry ; Sulfhydryl Compounds - metabolism ; Sulfhydryl Compounds - pharmacology ; Surface Properties ; Up-Regulation
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abstractMetabolic 'oligosaccharide engineering' methods based on N-acetyl-D-mannosamine (ManNAc) analogs allow the glycocalyx of living cells to be remodeled. Herein we report the analog Ac5ManNTGc (1) that enables thiols to be expressed in surface sialic acids. By locating this versatile functional group on the outer periphery of normally nonadhesive human Jurkat cells, we obtained spontaneous cell-cell clustering and attachment to complementary maleimide-derivatized substrates. When analyzed in human embryoid body-derived (hEBD) stem cells, Ac5ManNTGc induced β-catenin expression and altered cell morphology, consistent with neuronal differentiation. Notably, these effects were modulated by the growth substrate of the cells, with a stronger response observed on a gold surface than on glass. Together, these results establish sugar analogs as small-molecule tools for tissue engineering by providing a method for attaching cells to scaffolds via their surface carbohydrates as well as offering a means to influence stem cell fates.
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