302. Anhydrocarboxy-derivatives of hydroxy- and mercapto-acids

Davies, W. H.

doi:10.1039/jr9510001357

Cited by 34 publications

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“…A similar strategy was used for the synthesis of a Neu5Gc8Me-containing tetrasaccharide building block of the pentasaccharide component, Neu5Gc8Meα2–3(Neu5Gc8Meα2–6)GalNAcβ1–3Galβ1–4Glc, in GAA-7 ganglioside (100). In addition to the use of acetoxyacetyl chloride as a reagent for introducing a protected glycolyl group to the amino group on neuraminic acid (Neu) residue for the formation of Neu5Gc, 1,3-dioxolan-2,4-dione (101) prepared from glycolic acid was also used for the formation of Neu5Gc-GM1 ganglioside directly from naturally more abundant Neu5Ac version of GM1 (102).…”

Section: Chemical Synthesis Of Neu5gc-containing Oligosaccharidesmentioning

confidence: 99%

Synthesis of N-Glycolylneuraminic Acid (Neu5Gc) and Its Glycosides

Kooner

Chen

2019

Front. Immunol.

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Sialic acids constitute a family of negatively charged structurally diverse monosaccharides that are commonly presented on the termini of glycans in higher animals and some microorganisms. In addition to N -acetylneuraminic acid (Neu5Ac), N -glycolyl neuraminic acid (Neu5Gc) is among the most common sialic acid forms in nature. Nevertheless, unlike most animals, human cells loss the ability to synthesize Neu5Gc although Neu5Gc-containing glycoconjugates have been found on human cancer cells and in various human tissues due to dietary incorporation of Neu5Gc. Some pathogenic bacteria also produce Neu5Ac and the corresponding glycoconjugates but Neu5Gc-producing bacteria have yet to be found. In addition to Neu5Gc, more than 20 Neu5Gc derivatives have been found in non-human vertebrates. To explore the biological roles of Neu5Gc and its naturally occurring derivatives as well as the corresponding glycans and glycoconjugates, various chemical and enzymatic synthetic methods have been developed to obtain a vast array of glycosides containing Neu5Gc and/or its derivatives. Here we provide an overview on various synthetic methods that have been developed. Among these, the application of highly efficient one-pot multienzyme (OPME) sialylation systems in synthesizing compounds containing Neu5Gc and derivatives has been proven as a powerful strategy.

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Section: Chemical Synthesis Of Neu5gc-containing Oligosaccharidesmentioning

confidence: 99%

Synthesis of N-Glycolylneuraminic Acid (Neu5Gc) and Its Glycosides

Kooner

Chen

2019

Front. Immunol.

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“…In 1951 Davies first reported the synthesis of OCA by reacting α–hydroxy acid with phosgene, similar to NCA synthesis (Davies, 1951). To date, various OCAs have been synthesized (Figure 1B).…”

Section: Oca Monomer: Synthesis and Purificationmentioning

confidence: 99%

Living Ring-Opening Polymerization of O-Carboxyanhydrides: The Search for Catalysts

Zhong

Tong

2018

Front. Chem.

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Biodegradable poly(α-hydroxy acids) can be synthesized by means of ring-opening polymerization (ROP) of O-carboxyanhydrides (OCAs). Numerous catalysts have been developed to control the living polymerization of OCAs. Here we review the rationale for the use of OCA, the desirable features for and important attributes of catalysts for the ROP of OCAs, and specific examples that have been developed.

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“…In 1951, Davies first demonstrated the preparation of OCAs by the reaction of α‐hydroxy acid with phosgene, similar to the synthesis of N ‐carboxyanhydrides (NCAs). [ 43 ] OCAs are typically synthesized from α‐hydroxy acids by carbonylation using phosgene, diphosgene or triphosgene. Because of the structural similarity between α‐amino acids and α‐hydroxy acids, much effort has been made to prepare new OCAs from amino acids.…”

Section: Synthesis and Purification Of O‐carboxyanhydride Monomersmentioning

confidence: 99%

Synthesis of Sustainable Polyesters via Organocatalytic Ring‐Opening Polymerization of O‐carboxyanhydrides: Advances and Perspectives

Wang

Tao

2020

Macromol. Rapid Commun.

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Sustainable polyesters can be furnished via ring‐opening polymerization (ROP) of O‐carboxyanhydrides (OCAs). Various catalysts, especially metal‐based catalysts, are devised to achieve controlled ROP of OCAs. In the following mini review, the recent progress on the organocatalytic ROP of OCAs, including the usage of thiourea‐based bifunctional single‐molecule organocatalysts for eliminating epimerization in OCAs polymerization is summarized. Moreover, the future development of the organocatalytic ROP of OCAs for the synthesis of sustainable polyesters will be discussed.

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302. Anhydrocarboxy-derivatives of hydroxy- and mercapto-acids

Cited by 34 publications

References 0 publications

Synthesis of N-Glycolylneuraminic Acid (Neu5Gc) and Its Glycosides

Synthesis of N-Glycolylneuraminic Acid (Neu5Gc) and Its Glycosides

Living Ring-Opening Polymerization of O-Carboxyanhydrides: The Search for Catalysts

Synthesis of Sustainable Polyesters via Organocatalytic Ring‐Opening Polymerization of O‐carboxyanhydrides: Advances and Perspectives

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