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Iminosugars Section




Contribution to iminosugars field:

In May 1991 I was working on my degree thesis in organic chemistry and I was stuck in the synthesis of the molecule 9, when I get the molecule 10 thanks to serendipity.
This research earned me a coffee and thirty years of article citations.

thesis_page23 (1991)
thesis_page24 (1991)
thesis_page50 (1991)
thesis_page56 (1991)
thesis_page57 (1991)
thesis_page58 (1991)

Poster published on 28 May 1992

cover (1992)
poster (1992)

In 1993 the research group published the article about azasugars (also known as iminosugars):

Lay L., Nicotra F., Paganini A., Pangrazio C., Panza L.
A new procedure for the synthesis of azasugars
(1993) Tetrahedron Letters, 34 (28), pp. 4555-4558.

A new procedure for the synthesis of azasugars
Documents that cite the paper


Nicotra_approach.png

These authors have shown, for the first time, that the addition of Grignard reagents to N-benzyl and N-alkyl glycosylamines derived from perbenzylated pentofuranoses or hexopyranoses followed by a simple cyclization procedure afforded a short and convenient approach to imino-C-glycosides in the pyrrolidine and piperidine series [43,44]. The procedure is illustrated in Scheme 2 (see compounds 16) from a d-arabinofuranosylamine, using octylmagnesium bromide, and from a d-glucopyranosylamine using allylmagnesium bromide, and cyclization promoted by reacting the intermediate amino alditol with triflic anhydride.

Nicotra_approach.png

A first application of this reaction to the synthesis of azasugars was described in 1993 by the same authors, which opened the route to a new and efficient synthetic procedure towards this type of compounds.

This observation opened the way to an easy formation of azasugars following the sequence of a ) glycosylamine formation, b) Grignard reaction. and c ) cyclization with Tf2O. This procedure is easily extended to include pyranose rings.

For a review of the procedure, see:

Addition of organometallics to aldimines, aldoximes and aldononitriles: a key step towards the synthesis of azasugars

Glycoside Mimics from Glycosylamines: Recent Progress

It is amazing that such a small change replacing an oxygen atom in a sugar molecule with a nitrogen atom can have wide ranging therapeutic benefits.

Iminosugars: small molecules with big potential

Iminosugar antivirals: the therapeutic sweet spot

Repurposing of Miglustat to inhibit the coronavirus Severe Acquired Respiratory Syndrome SARS-CoV-2

The iminosugars celgosivir, castanospermine and UV-4 inhibit SARS-CoV-2 replication

Iminosugars With Endoplasmic Reticulum alpha-Glucosidase Inhibitor Activity Inhibit ZIKV Replication and Reverse Cytopathogenicity in vitro

Sirona Biochem

Tuning the activity of iminosugars

Glucosidase inhibitors suppress SARS-CoV-2 in tissue culture

Inhibitors of Protein Glycosylation Are Active against the Coronavirus Severe Acute Respiratory Syndrome Coronavirus SARS-CoV-2




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