Novel proteoglycan glycotechnology: chemoenzymatic synthesis of chondroitin sulfate-containing molecules and its application

Yamaguchi, Masanori; Takagaki, Keiichi; Kojima, Kaoru; Hayashi, Naohiro; Chen, Fengchao; Kakizaki, Ikuko; Kon, Atsushi; Endo, Masahiko

doi:10.1007/s10719-009-9252-y

Cited by 10 publications

(6 citation statements)

References 35 publications

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“…By treating CS‐serine with endo ‐β‐xylosidase in the presence of propargyl alcohol, an alkyne‐terminated CS chain was obtained. It was employed in CuAAC reactions with several azide‐labeled molecules to achieve proteoglycan mimics or fragments thereof , …”

Section: Chondroitin Sulfate Fucosylated Chondroitin Sulfate Andmentioning

confidence: 99%

Chemical Derivatization of Sulfated Glycosaminoglycans

2016

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Sulfated glycosaminoglycans (GAGs) are a family of complex polysaccharides ubiquitously distributed in extracellular matrices and at cell surfaces and playing key roles in a myriad of biological processes. Their structures are based on disaccharide building blocks, usually containing an amino sugar and an uronic acid, decorated with one or more sulfate groups. Many efforts to gain access to a large number of sulfated GAG polysaccharides with potential tailored biomedical applications, usually based on suitable chemical (and chemo-enzymatic) derivatization procedures that modified the native polysaccharide structures, have been reported in the last two decades. In this review we survey such reactions on the basis of (i) the sulfated GAG substrate [(fucosylated) chondroitin sulfate, dermatan sulfate, heparin, and heparan sulfate], and (ii) the sort of structural modification (sulfation pattern modification, oxidation, carboxy group derivatization, N- and O-acylation, reducing-end functionalization)

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Section: Chondroitin Sulfate Fucosylated Chondroitin Sulfate Andmentioning

confidence: 99%

Chemical Derivatization of Sulfated Glycosaminoglycans

2016

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“…Another ChS-conjugated therapeutic peptides and proteins can be made to acquire resistance to proteolysis, which would improve their performance as medicines from two viewpoints (Figure 38) [55]. First, their resistance to proteolysis would extend their biological halflife, and second, their binding to specific tissues would enable them to deliver drugs precisely to a target site.…”

Section: Modification Of Positionmentioning

confidence: 99%

Polysaccharides: The “Click” Chemistry Impact

et al. 2011

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Polysaccharides are complex but essential compounds utilized in many areas such as biomaterials, drug delivery, cosmetics, food chemistry or renewable energy. Modifications and functionalizations of such polymers are often necessary to achieve molecular structures of interest. In this area, the emergence of the "click" chemistry concept, and particularly the copper-catalyzed version of the Huisgen 1,3-dipolar cycloaddition reaction between terminal acetylenes and azides, had an impact on the polysaccharides chemistry. The present review summarizes the contribution of "click" chemistry in the world of polysaccharides.

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“…The peptide-GAG hydrogels investigated in this work are thought to be a reasonable minimal imitation of the proteoglycan filaments of extracellular matrices that provide the mechanical structure in soft tissues. [52][53][54] By controlling the duration of hydrodynamic shear forces during the gelation process, we can vary the stiffness of these gels by up to two orders of magnitude at fixed composition. Therefore, composition and mechanics can be individually selected over a broad range of accessible shear moduli.…”

Section: Discussionmentioning

confidence: 99%

Hydrodynamic Mixing Tunes the Stiffness of Proteoglycan‐Mimicking Physical Hydrogels

Warren

Miles

Kapur

et al. 2021

Adv Healthcare Materials

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Self-assembling hydrogels are promising materials for regenerative medicine and tissue engineering. However, designing hydrogels that replicate the 3-4 order of magnitude variation in soft tissue mechanics remains a major challenge. Here hybrid hydrogels are investigated formed from short self-assembling -fibril peptides, and the glycosaminoglycan chondroitin sulfate (CS), chosen to replicate physical aspects of proteoglycans, specifically natural aggrecan, which provides structural mechanics to soft tissues. Varying the peptide:CS compositional ratio (1:2, 1:10, or 1:20) can tune the mechanics of the gel by one to two orders of magnitude. In addition, it is demonstrated that at any fixed composition, the gel shear modulus can be tuned over approximately two orders of magnitude through varying the initial vortex mixing time. This tuneability arises due to changes in the mesoscale structure of the gel network (fibril width, length, and connectivity), giving rise to both shear-thickening and shear-thinning behavior. The resulting hydrogels range in shear elastic moduli from 0.14 to 220 kPa, mimicking the mechanical variability in a range of soft tissues. The high degree of discrete tuneability of composition and mechanics in these hydrogels makes them particularly promising for matching the chemical and mechanical requirements of different applications in tissue engineering and regenerative medicine.

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Novel proteoglycan glycotechnology: chemoenzymatic synthesis of chondroitin sulfate-containing molecules and its application

Cited by 10 publications

References 35 publications

Chemical Derivatization of Sulfated Glycosaminoglycans

Chemical Derivatization of Sulfated Glycosaminoglycans

Polysaccharides: The “Click” Chemistry Impact

Hydrodynamic Mixing Tunes the Stiffness of Proteoglycan‐Mimicking Physical Hydrogels

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