Synthesis of glycosylamides and 4-N-glycosyl-l-asparagine derivatives

Khorlin, A. Ya.; Zurabyan, S. E.; Macharadze, R. G.

doi:10.1016/s0008-6215(00)84671-6

Cited by 47 publications

(9 citation statements)

References 16 publications

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“…2‐Acetamido‐ N ‐acetyl‐3,4,6‐tri‐ O ‐acetyl‐2‐deoxy‐β‐ D ‐glucopyranosylamine (18): Isolated as a solid with m.p. 235 °C (dec.) (ref 35. 240−241 °C and ref 53.…”

Section: Methodsmentioning

confidence: 99%

“…244−246 °C); [α] D = +18 ( c = 0.5, pyridine) [ref 53. +41 ( c = 1, chloroform) and ref 35. +22 ( c = 0.5, pyridine)].…”

Section: Methodsmentioning

confidence: 99%

“…2,3,4,6‐Tetra‐ O ‐acetyl‐ N ‐[1‐benzyl‐ N ‐(benzyloxy)carbonyl‐ L ‐aspart4‐oyl]‐β‐ D ‐glucopyranosylamine (36): Isolated as a solid with m.p. 142° C (ref 35. 143.5−144 °C); [α] D = +19 ( c = 1, chloroform) [ref 35.…”

Section: Methodsmentioning

confidence: 99%

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Synthesis of Glycosylamines from Glycosyl Isothiocyanates and Bis(tributyltin) Oxide

et al. 2001

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“…2‐Acetamido‐ N ‐acetyl‐3,4,6‐tri‐ O ‐acetyl‐2‐deoxy‐β‐ D ‐glucopyranosylamine (18): Isolated as a solid with m.p. 235 °C (dec.) (ref 35. 240−241 °C and ref 53.…”

Section: Methodsmentioning

confidence: 99%

“…244−246 °C); [α] D = +18 ( c = 0.5, pyridine) [ref 53. +41 ( c = 1, chloroform) and ref 35. +22 ( c = 0.5, pyridine)].…”

Section: Methodsmentioning

confidence: 99%

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Synthesis of Glycosylamines from Glycosyl Isothiocyanates and Bis(tributyltin) Oxide

et al. 2001

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“…[83] An alternative method for the synthesis of the b-N-glycosidic bond involves glycosyl isothiocyanates that are readily available through the reaction of glycosyl halides with potassium rhodanide. [84] Günther and Kunz applied this method to the synthesis of b-mannosylchitobiosyl asparagine, a compound that comprises the central trisaccharide core of Nglycoproteins. [85] For the synthesis of more complex N-glycans, the introduction of the carbohydrate moiety is commonly performed by using a block condensation of the full-length glycosylamine with the aspartic acid derivative.…”

Section: Synthesis Of Preformed Glycosyl Amino Acidsmentioning

confidence: 99%

Glycopeptide Synthesis and the Effects of Glycosylation on Protein Structure and Activity

Seitz

2000

ChemBioChem

197

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Despite the omnipresence of protein glycosylation in nature, little is known about how the attachment of carbohydrates affects peptide and protein activity. One reason is the lack of a straightforward method to access biologically relevant glycopeptides and glycoproteins. The isolation of homogeneous glycopeptides from natural sources is complicated by the heterogeneity of naturally occuring glycoproteins. It is chemical and chemoenzymatic synthesis that is meeting the challenge to solve this availability problem, thus playing a key role for the advancement of glycobiology. The current art of glycopeptide synthesis, albeit far from being routine, has reached a level of maturity that allows for the access to homogeneous and pure material for biological and medicinal research. Even the ambitious goal of the total synthesis of an entire glycoprotein is within reach. It is demonstrated that with the help of synthetic glycopeptides the effects of glycosylation on protein structure and function can be studied in molecular detail. For example, in immunology, synthetic (tumour-specific) glycopeptides can be used as immunogens to elicit a tumour-cell-specific immune response. Again, synthetic glycopeptides are an invaluable tool to determine the fine specificity of the immune response that can be mediated by both carbohydrate-specific B and T cells. Furthermore, selected examples for the use of synthetic glycopeptides as ligands of carbohydrate-binding proteins and as enzyme substrates or inhibitors are presented.

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“…Other methods includes the reaction of acyl glycosyl isothiocyanates with carboxylic acids catalyzed by trimethylamine . In the case of the less abundant α‐glycosylamides a standard procedure for its preparation employs a traceless Staudinger ligation with diphenylphosphanyl‐phenyl ethers and α‐glycosyl azides …”

Section: Introductionmentioning

confidence: 99%

Direct Coupling of Amides and Urea to Glycosyl Halides Using Silver Triflate

et al. 2016

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Abstract:We herein report the coupling of various amides and ureas to glycosyl halides in the presence of silver triflate at room temperature. A 1:1 mixture of α/ diastereomers was obtained when alkyl/heteroaryl amides and substituted ureas were added to gluco and galacto haloglycosides. The effect of temperature, halogen, protecting group of the sugar and substituent of the amide in the overall yields and stereoselectivity

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Synthesis of glycosylamides and 4-N-glycosyl-l-asparagine derivatives

Cited by 47 publications

References 16 publications

Synthesis of Glycosylamines from Glycosyl Isothiocyanates and Bis(tributyltin) Oxide

Synthesis of Glycosylamines from Glycosyl Isothiocyanates and Bis(tributyltin) Oxide

Glycopeptide Synthesis and the Effects of Glycosylation on Protein Structure and Activity

Direct Coupling of Amides and Urea to Glycosyl Halides Using Silver Triflate

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