Formation of 1,5-Dideoxy-1,5-iminohexitols on Borohydride Reduction of 2-Amino-2-deoxyhexofuranurono-6,3-lactones.

Leontein, Karin; Lindberg, Bengt; Lōnngren, Jörgen; Napier, Russell J.; Thomson, R. H.; Tezuka, Takahiro

doi:10.3891/acta.chem.scand.36b-0515

Cited by 33 publications

(9 citation statements)

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“…1‐Deoxy‐L‐gulonojirimycin 30 (L‐ gulo ‐DNJ) represents a rare example of naturally occurring DNJ analogue belonging to the L‐family [15a] . It was initially identified as D‐ gulo ‐DNJ ( ent ‐ 30 ) and not as L‐ gulo ‐DNJ 30 [15b] .…”

Section: Sulfonamido Hydroxylation Of 346‐tri‐o‐benzyl‐d‐glucal and Its Synthetic Applicationsmentioning

confidence: 99%

From Glycals to Nitrogen Heterocycles and Carbocycles via “Cleavage‐Intramolecular Recombination Strategy”

Ramesh

2021

The Chemical Record

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Glycals (carbohydrate enol‐ethers) have enjoyed profound applications in organic synthesis for more than a century. They not only serve as versatile glycosyl donors or as substrates for Ferrier rearrangement, but also find extensive synthetic applications especially as a “chiral pool” for accomplishing the synthesis of a variety of natural and biologically important compounds. As cyclic enol ethers, they demonstrate high reactivity and are among the most and variously transformable monosaccharide derivatives. The uniqueness of the reactivity of glycals is that they can be synthetically tuned to get a library of derivatives through stereo‐ and regioselective introduction of a variety of functional groups at C1, C2, C3 as well as C4 carbons of the sugar. We have developed a practical approach for stereoselective mono‐ and diamination of glycals and over the years utilized these scaffolds for the synthesis of a variety of biologically important nitrogen heterocycles and carbocycles through a “Diversity Oriented Approach”. Our synthetic strategy in this direction mainly relied on the cleavage of ring O−C bond of the sugar followed by an “intramolecular recombination” reaction. Utilizing this strategy, we have accomplished the synthesis of several biologically important natural products, their analogues and related unnatural derivatives. Examples of such compounds reported from our group include polyhydroxypyrrolidines, DMDP, anisomycin, steviamine, pochonicine, conduramines, bulgecinine, aminocyclitols, azepanes, 4‐hydroxy‐D‐proline, azanucleosides and their analogues. A personal account highlighting these syntheses is presented here.

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Section: Sulfonamido Hydroxylation Of 346‐tri‐o‐benzyl‐d‐glucal and Its Synthetic Applicationsmentioning

confidence: 99%

From Glycals to Nitrogen Heterocycles and Carbocycles via “Cleavage‐Intramolecular Recombination Strategy”

Ramesh

2021

The Chemical Record

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“…De-O-acetylation of ECA was performed in 0.25 M NaOH at 56°C for 1 h; then the reaction mixture was neutralized with 1 M HC1. Uronic acid content was determined according to Leontein et aL [6]; carboxyl reduction of ECA was performed using the method of Taylor et al [7].…”

Section: Chemical Modification Of Eca and Preparation Of Oligosaccharmentioning

confidence: 99%

Characterization of an enterobacterial common antigen (ECA) epitope recognized by anti-ECA-tetanus toxoid conjugate serum

Ługowski

1991

FEMS Microbiology Letters

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The antigenic reactivity of both native and chemically modified enterobacterial common antigen (ECA) with anti-ECA-tetanus toxoid (TT) conjugate serum was investigated. The results obtained suggest that reduction of the carboxyl group of the mannosaminuronic acid component of ECA diminishes, but does not destroy its antigenic reactivity. Each of the sugar components were found to contribute to its reactivity with anti-ECA-TT conjugate serum, indicating that the trisaccharide repeating unit represents the ECA epitope. A nonasaccharide (trimer of the ECA repeating unit) inhibited antibody binding better than the hexasaccharide dimer, a finding which suggests that oligosaccharide conformation also makes a contribution to its inhibitory activity.

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“…Uronic acid content was determined according to Leontein et aL [6]; carboxyl reduction of ECA was performed using the method of Taylor et al [7]. Uronic acid content was determined according to Leontein et aL [6]; carboxyl reduction of ECA was performed using the method of Taylor et al [7].…”

Section: Chemical Modification Of Eca and Preparation Of Oligosaccharmentioning

confidence: 99%

Characterization of an enterobacterial common antigen (ECA) epitope recognized by anti-ECA-tetanus toxoid conjugate serum

Ługowski

Romanowska

1991

FEMS Microbiology Letters

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Summary The antigenic reactivity of both native and chemically modified enterobacterial common antigen (ECA) with anti‐ECA‐tetanus toxoid (TT) conjugate serum was investigated. The results obtained suggest that reduction of the carboxyl group of the mannosaminuronic acid component of ECA diminishes, but does not destroy its antigenic reactivity. Each of the sugar components were found to contribute to its reactivity with anti‐ECA‐TT conjugate serum, indicating that the trisaccharide repeating unit represents the ECA epitope. A nonasaccharide (trimer of the ECA repeating unit) inhibited antibody binding better than the hexasaccharide dimer, a finding which suggests that oligosaccharide conformation also makes a contribution to its inhibitory activity.

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Formation of 1,5-Dideoxy-1,5-iminohexitols on Borohydride Reduction of 2-Amino-2-deoxyhexofuranurono-6,3-lactones.

Cited by 33 publications

References 0 publications

From Glycals to Nitrogen Heterocycles and Carbocycles via “Cleavage‐Intramolecular Recombination Strategy”

From Glycals to Nitrogen Heterocycles and Carbocycles via “Cleavage‐Intramolecular Recombination Strategy”

Characterization of an enterobacterial common antigen (ECA) epitope recognized by anti-ECA-tetanus toxoid conjugate serum

Characterization of an enterobacterial common antigen (ECA) epitope recognized by anti-ECA-tetanus toxoid conjugate serum

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