Synthesis and Application of Glycopeptide and Glycoprotein Mimetics

Specker, Daniel; Wittmann, Valentin

doi:10.1007/128_2006_104

Cited by 44 publications

(28 citation statements)

References 234 publications

(266 reference statements)

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“…1B) are two common chemical strategies for the synthesis of N- or O-linked glycopeptides. In the direct method, the pre-synthesised glycosylated amino acid is coupled to the elongating peptide using solid phase peptide synthesis (SPPS) in a stepwise fashion 28. Two methods, fluorenylmethyloxycarbonyl (Fmoc) and tert -butyloxycarbonyl (Boc) chemistry, are used in SPPS.…”

Section: Glycosylation Strategy For Peptide Deliverymentioning

confidence: 99%

Glycosylation, an effective synthetic strategy to improve the bioavailability of therapeutic peptides

et al. 2016

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Section: Glycosylation Strategy For Peptide Deliverymentioning

confidence: 99%

Glycosylation, an effective synthetic strategy to improve the bioavailability of therapeutic peptides

et al. 2016

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“…In addition to useful but polydisperse multivalent glycomimetics of prominent components at the surfaces of mammalian cells [such as neoglycoproteins, 28,29 neoglycopeptides, [30][31][32] neoglycolipids (or glycoliposomes), 33,34 glycopolymers, [35][36][37][38] or glyconoparticles, [39][40][41][42][43][44][45][46][47][48][49] new synthetic families of well-defined and monodisperse glycosylated macromolecules have recently emerged, including glycoclusters, such glycosylated nanomaterials as glycofullerenes and glyconanotubes, glycosylated architectures from supramolecular assembly processes, and finally glycodendrimers. The uniformity of these multivalent neoglycoconjugates is ensured by the controlled arrangement of the constitutional building blocks.…”

Section: Synthesis and Applications Of Multivalent Glycoconjugatesmentioning

confidence: 99%

Design and Creativity in Synthesis of Multivalent Neoglycoconjugates

Chabre

Roy

2010

Advances in Carbohydrate Chemistry and Biochemistry

309

208

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From the authors' opinion, this chapter constitutes a modest extension of the seminal and inspiring contribution of Stowell and Lee on neoglycoconjugates published in this series [C. P. Stowell and Y. C. Lee, Adv. Carbohydr. Chem. Biochem., 37 (1980) 225-281]. The outstanding progresses achieved since then in the field of the "glycoside cluster effect" has witnessed considerable creativity in the design and synthetic strategies toward a vast array of novel carbohydrate structures and reflects the dynamic activity in the field even since the recent chapter by the Nicotra group in this series [F. Nicotra, L. Cipolla, F. Peri, B. La Ferla, and C. Radaelli, Adv. Carbohydr. Chem. Biochem., 61 (2007) 353-398]. Beyond the more classical neoglycoproteins and glycopolymers (not covered in this work) a wide range of unprecedented and often artistically beautiful multivalent and monodisperse nanostructures, termed glycodendrimers for the first time in 1993, has been created. This chapter briefly surveys the concept of multivalency involved in carbohydrate-protein interactions. The topic is also discussed in regard to recent steps undertaken in glycobiology toward identification of lead candidates using microarrays and modern analytical tools. A systematic description of glycocluster and glycodendrimer synthesis follows, starting from the simplest architectures and ending in the most complex ones. Presentation of multivalent glycostructures of intermediate size and comprising, calix[n]arene, porphyrin, cyclodextrin, peptide, and carbohydrate scaffolds, has also been intercalated to better appreciate the growing synthetic complexity involved. A subsection describing novel all-carbon-based glycoconjugates such as fullerenes and carbon nanotubes is inserted, followed by a promising strategy involving dendrons self-assembling around metal chelates. The chapter then ends with those glycodendrimers that have been prepared using commercially available dendrimers possessing varied functionalities, or systematically synthesized using either divergent or convergent strategies.

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“…7,8 Avoiding disruption to the structural integrity of the PS remains one of main challenges when devising a conjugation strategy, since bacterial PSs usually do not express functional groups that can be readily used in the formation of a covalent bond to the protein. In traditional methods, the PS or/ and protein is modified first, followed sometimes by the addition of a spacer, and subsequently joined via several reaction types.…”

Section: B S T R a C Tmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

“…In traditional methods, the PS or/ and protein is modified first, followed sometimes by the addition of a spacer, and subsequently joined via several reaction types. 6,7,[9][10][11] The formation of aldehyde moieties in the PS by controlled periodate oxidation, followed by conjugation to the protein by reductive amination, 12 has been one of the most industrious methods by which commercially available PS-conjugate vaccines have been synthesized.In this article we present a new scheme to conjugate PSs to carrier proteins utilizing 2,2,6,6-tetramethylpiperidin-1-oxyl (TEM-PO)-mediated oxidation. TEMPO selectively oxidizes primary alcohols to carboxylic acids, and it has been commonly used in the oxidation of a wide range of organic compounds after Golubev's first successful attempt in the mid-1960s.…”

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