Trichloroacetimidates

Schmidt, Richard R.; Jung, Karl‐Heinz

doi:10.1002/9783527618255.ch2

Cited by 48 publications

(19 citation statements)

References 211 publications

(64 reference statements)

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“…[55] To date, most glycosyl iodides used for glycoside synthesis have been protected with arming (activating) protecting groups (typically O-benzyl or electrondonating groups), although disarmed (deactivated) glucuronyl iodides, with electron-withdrawing groups on the pyranose ring, also proved to be efficient donors in b-glucuronylation reactions of a range of steroidal alcohols. [56] The reaction of the pivaloylated glucuronyl iodide 7 with 3-Opivaloylmorphine (8) in the presence of iodine afforded the 1,2-trans glycoside stereospecifically in 55 % yield; subseScheme 1. Glycoside syntheses with glycosyl iodides as donors.…”

Section: Glycosyl Iodidesmentioning

confidence: 99%

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New Principles for Glycoside‐Bond Formation

2009

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Increased understanding of the important roles that oligosaccharides and glycoconjugates play in biological processes has led to a demand for significant amounts of these materials for biological, medicinal, and pharmacological studies. Therefore, tremendous effort has been made to develop new procedures for the synthesis of glycosides, whereby the main focus is often the formation of the glycosidic bonds. Accordingly, quite a few review articles have been published over the past few years on glycoside synthesis; however, most are confined to either a specific type of glycoside or a specific strategy for glycoside synthesis. In this Review, new principles for the formation of glycoside bonds are discussed. Developments, mainly in the last ten years, that have led to significant advances in oligosaccharide and glycoconjugate synthesis have been compiled and are evaluated.

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Section: Glycosyl Iodidesmentioning

confidence: 99%

“…[4a, 5,[7][8][9][10] Other approaches closely related to the Koenigs-Knorr method have been investigated extensively. The exchange of the anomeric oxygen atom for a fluorine, alkylthio, or arylthio leaving group found great interest, as these groups are not affected by manipulations of orthogonal protecting groups (see Section 2.2).…”

Section: Introductionmentioning

confidence: 99%

New Principles for Glycoside‐Bond Formation

2009

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“…26À28 Carboxylmethyl-dimannose was obtained by ozonolysis of the alkene, 29 followed by further oxidation with Jones reagent. 26 Global deprotection under Birch reduction 30 furnished the fully deprotected α-1,2-linked dimannose ( Figure 1B).…”

Section: Abstract: Polyanhydrides Nanoparticles Carbohydrates Dendmentioning

confidence: 99%

Mannose-Functionalized “Pathogen-like” Polyanhydride Nanoparticles Target C-Type Lectin Receptors on Dendritic Cells

et al. 2011

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Targeting pathogen recognition receptors on dendritic cells (DCs) offers the advantage of triggering specific signaling pathways to induce a tailored and robust immune response. In this work, we describe a novel approach to targeted antigen delivery by decorating the surface of polyanhydride nanoparticles with specific carbohydrates to provide "pathogen-like" properties that ensure nanoparticles engage C-type lectin receptors on DCs. The surface of polyanhydride nanoparticles was functionalized by covalent linkage of dimannose and lactose residues using an amine-carboxylic acid coupling reaction. Coculture of functionalized nanoparticles with bone marrow-derived DCs significantly increased cell surface expression of MHC II, the T cell costimulatory molecules CD86 and CD40, the C-type lectin receptor CIRE and the mannose receptor CD206 over the nonfunctionalized nanoparticles. Both nonfunctionalized and functionalized nanoparticles were efficiently internalized by DCs, indicating that internalization of functionalized nanoparticles was necessary but not sufficient to activate DCs. Blocking the mannose and CIRE receptors prior to the addition of functionalized nanoparticles to the culture inhibited the increased surface expression of MHC II, CD40 and CD86. Together, these data indicate that engagement of CIRE and the mannose receptor is a key mechanism by which functionalized nanoparticles activate DCs. These studies provide valuable insights into the rational design of targeted nanovaccine platforms to induce robust immune responses and improve vaccine efficacy. The use of vaccine adjuvants to activate the innate immune system is crucial to vaccine effectiveness. 1 Adjuvants can be used to enhance the efficacy of single dose vaccines and reduce the required antigen dose. The use of biodegradable polymer nanoparticles as vaccine delivery vehicles allows for effective delivery of payloads by parental or mucosal administration by protecting the antigen from harsh physiological conditions and enabling transport across biological barriers (e.g., mucus membranes). 2 Polyanhydride nanoparticles have shown excellent potential as vaccine carriers. 3À6 Encapsulation of protein antigens into polyanhydride particles stabilizes them and provides sustained azntigen release; 4,7 these particles also enhance the immune response by acting as an adjuvant. 3 Dendritic cells (DCs) are antigen presenting cells (APCs) that play a major role in connecting the innate and adaptive immune systems, a key step to inducing protective immunity. 8 DCs can sense and internalize antigen by a variety of mechanisms that trigger DC maturation and direct further interactions with other immune cells, including naive T cells. 1,9,10 Pattern recognition receptors (PRRs) on DCs detect the presence of a potential threat by interacting with pathogen-associated molecular patterns (PAMPs). 10,11 In particular, C-type lectin receptors (CLRs) are PRRs with highly conserved carbohydrate-recognition domains that bind sugar moieties (e.g., mannose, fuco...

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“…In the molecular engineering of carbohydrates, glycosyl trichloroacetimidates play an important role as effective glycosyl donor molecules; they are generally prepared by trapping anomeric alcohols by treatment with trichloroacetonitrile in the presence of a strong base [73]. However, purification is sometimes diminished by the acid lability of trichloroacetimidate functionalities.…”

Section: Miscellaneousmentioning

confidence: 99%

Polymer‐Supported Organosuperbases

Kotsuki

2009

Superbases for Organic Synthesis

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Trichloroacetimidates

Cited by 48 publications

References 211 publications

New Principles for Glycoside‐Bond Formation

New Principles for Glycoside‐Bond Formation

Mannose-Functionalized “Pathogen-like” Polyanhydride Nanoparticles Target C-Type Lectin Receptors on Dendritic Cells

Polymer‐Supported Organosuperbases

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