Hydrazine derivatives of carbohydrates and related compounds

Khadem, Hassan S. El; Fatiadi, Alexander J.

doi:10.1016/s0065-2318(00)55006-9

Cited by 16 publications

(5 citation statements)

References 535 publications

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“…However, we did detect a molecular ion shifted 2 Da lower. We suspect that this is due to subsequent oxidation of the phenylhydrazone at the C2 position as has been previously reported as an intermediate in the synthesis of osazones . We have also observed molecular ions consistent with the same oxidized phenylhydrazones for standards prepared from free GalNAc and galactose prepared using the same method.…”

Section: Methodssupporting

confidence: 85%

Discovery and Development of Promiscuous O-Glycan Hydrolases for Removal of Intact Sialyl T-Antigen

et al. 2021

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Mucin-type O-glycosylation (O-glycosylation) is a common posttranslational modification that confers distinct biophysical properties to proteins and plays crucial roles in intercellular signaling. Yet, despite the importance of Oglycans, relatively few tools exist for their analysis and modification. In particular, there is a need for enzymes that can cleave the wide range of O-glycan structures found on protein surfaces, to facilitate glycan profiling and editing. Through functional metagenomic screening of the human gut microbiome, we discovered endo-O-glycan hydrolases from CAZy family GH101 that are capable of slowly cleaving the intact sialyl T-antigen trisaccharide (a ubiquitous O-glycan structure in humans) in addition to their primary activity against the T-antigen disaccharide. We then further explored this sequence space through phylogenetic profiling and analysis of representative enzymes, revealing large differences in the levels of this promiscuous activity between enzymes within the family. Through structural and sequence analysis, we identified active site residues that modulate specificity. Through subsequent rational protein engineering, we improved the activity of an enzyme identified by phylogenetic profiling sufficiently that substantial removal of the intact sialyl Tantigen from proteins could be readily achieved. Our best sialyl T-antigen hydrolase mutant, SpGH101 Q868G, is further shown to function on a number of proteins, tissues, and cells. Access to this enzyme opens up improved methodologies for unraveling the glycan code.

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Section: Methodssupporting

confidence: 85%

Discovery and Development of Promiscuous O-Glycan Hydrolases for Removal of Intact Sialyl T-Antigen

et al. 2021

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“… 24 , 25 , 27 , 28 The preference of adopting the open chain, cyclic structures, or an interconvertable equilibrated mixture of them has been synergistically effected by the basicity of hydrazines, reaction conditions, pH of the reaction mixture, solvent used in 1 H NMR spectra, as well as sugar configuration. 29 …”

Section: Resultsmentioning

confidence: 99%

“…The outcome of coupling of acylhydrazines or thioacylhydrazines with various reducing saccharides has been reported to exist in solution as sugar hydrazones (acyclic forms) − or glycosylhydrazides (cyclic forms) − and often coexist in tautomeric equilibrium mixtures. ,,, The preference of adopting the open chain, cyclic structures, or an interconvertable equilibrated mixture of them has been synergistically effected by the basicity of hydrazines, reaction conditions, pH of the reaction mixture, solvent used in 1 H NMR spectra, as well as sugar configuration …”

Section: Resultsmentioning

confidence: 99%

Synthesis and Antimicrobial Activity of 1,3,4-Oxadiazoline, 1,3-Thiazolidine, and 1,2,4-Triazoline Double-Tailed Acyclo C-Nucleosides

et al. 2022

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The condensation products of terphthaloyl bishydrazide with two equivalents of various monosaccharide aldoses were found to have a bis(sugarhydrazone) form or bis-glycosylhydrazide structure or coexist in tautomeric equilibrium depending on the sugar configuration. The condensation products were substantially utilized as 3-acetyl-1,3,4-oxadiazoline, 1,3-thiazolidine, and 4-amino-1,2,4-triazoline double-tailed acyclo C-nucleosides synthons. The preliminary antimicrobial activities of representative examples of the prepared compounds were evaluated.

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“…Glycosyl sulfoxides 1,2-Anhydro-sugars (R ¼ acetyl, benzoyl, benzyl) Glycosylamine derivatives are probably involved in the complex Maillard reaction [60], whereby sugars, amines, and amino acids (proteins) condense, rearrange, and degrade during cooking or the preservation of food. Hydrazones and osazones result when aldoses or ketoses are reacted with hydrazine or arylhydrazines, the product depending on the conditions used [81]. With hydrazine acetate in highly acidic medium in the cold, hydrazones are formed, which initially adopt the acyclic structure, but tautomerize in aqueous solution to the cyclic glycosylhydrazine forms.…”

Section: Glycosyl Trichloroacetimidates Thioglycosidesmentioning

confidence: 99%