1,5-Dideoxy-1,5-imino-D-mannitol

1,5-Dideoxy-1,5-imino-D-mannitol

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Category Enzyme inhibitors
Catalog number BBF-01389
CAS 146747-37-7
Molecular Weight 163.17
Molecular Formula C6H13NO4

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Description

It is produced by the strain of Streptomyces lavendulae GC-148.

Specification

Synonyms (-)-1-Deoxynojirimycin
IUPAC Name (2S,3S,4S,5R)-2-(hydroxymethyl)piperidine-3,4,5-triol
Canonical SMILES C1C(C(C(C(N1)CO)O)O)O
InChI InChI=1S/C6H13NO4/c8-2-3-5(10)6(11)4(9)1-7-3/h3-11H,1-2H2/t3-,4+,5-,6-/m0/s1
InChI Key LXBIFEVIBLOUGU-FSIIMWSLSA-N

Properties

Melting Point 187-188°C

Reference Reading

1. Synthesis of 1-Deoxymannojirimycin from d-Fructose using the Mitsunobu Reaction
Peter Sunde-Brown, Ian D Jenkins, Todd A Houston J Org Chem. 2022 Dec 16;87(24):16895-16901. doi: 10.1021/acs.joc.2c02174. Epub 2022 Dec 2.
Three different Mitsunobu reactions have been investigated for the synthesis of 1-deoxymannojirimycin (1-DMJ) from d-fructose. The highest yielding and most practical synthesis can be undertaken on a 10 g scale with minimal chromatography. In the key step, N,O-di-Boc-hydroxylamine reacts with methyl 1,3-isopropylidene-α-d-fructofuranose under Mitsunobu conditions to give 14. Acidic hydrolysis affords nitrone 15, which reduces quantitatively via catalytic hydrogenolysis to afford 1-DMJ (4) in 55% overall yield from d-fructose (cf. 37% for azide route and 29% for nosyl route).
2. Chaperone Therapy in Fabry Disease
Frank Weidemann, Ana Jovanovic, Ken Herrmann, Irfan Vardarli Int J Mol Sci. 2022 Feb 8;23(3):1887. doi: 10.3390/ijms23031887.
Fabry disease is an X-linked lysosomal multisystem storage disorder induced by a mutation in the alpha-galactosidase A (GLA) gene. Reduced activity or deficiency of alpha-galactosidase A (AGAL) leads to escalating storage of intracellular globotriaosylceramide (GL-3) in numerous organs, including the kidneys, heart and nerve system. The established treatment for 20 years is intravenous enzyme replacement therapy. Lately, oral chaperone therapy was introduced and is a therapeutic alternative in patients with amenable mutations. Early starting of therapy is essential for long-term improvement. This review describes chaperone therapy in Fabry disease.
3. Cardiac Involvement in Fabry Disease: JACC Review Topic of the Week
Maurizio Pieroni, James C Moon, Eloisa Arbustini, Roberto Barriales-Villa, Antonia Camporeale, Andreja Cokan Vujkovac, Perry M Elliott, Albert Hagege, Johanna Kuusisto, Aleš Linhart, Peter Nordbeck, Iacopo Olivotto, Päivi Pietilä-Effati, Mehdi Namdar J Am Coll Cardiol. 2021 Feb 23;77(7):922-936. doi: 10.1016/j.jacc.2020.12.024.
Fabry disease (FD) is a rare X-linked inherited lysosomal storage disorder caused by deficient α-galactosidase A activity that leads to an accumulation of globotriasylceramide (Gb3) in affected tissues, including the heart. Cardiovascular involvement usually manifests as left ventricular hypertrophy, myocardial fibrosis, heart failure, and arrhythmias, which limit quality of life and represent the most common causes of death. Following the introduction of enzyme replacement therapy, early diagnosis and treatment have become essential to slow disease progression and prevent major cardiac complications. Recent advances in the understanding of FD pathophysiology suggest that in addition to Gb3 accumulation, other mechanisms contribute to the development of Fabry cardiomyopathy. Progress in imaging techniques have improved diagnosis and staging of FD-related cardiac disease, suggesting a central role for myocardial inflammation and setting the stage for further research. In addition, with the recent approval of oral chaperone therapy and new treatment developments, the FD-specific treatment landscape is rapidly evolving.

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