An iminosugar, also known as an iminosaccharide, is any

analog Analog or analogue may refer to: Computing and electronics * Analog signal, in which information is encoded in a continuous variable ** Analog device, an apparatus that operates on analog signals *** Analog electronics, circuits which use analog ...

of a

sugar Sugar is the generic name for sweet-tasting, soluble carbohydrates, many of which are used in food. Simple sugars, also called monosaccharides, include glucose, fructose, and galactose. Compound sugars, also called disaccharides or double ...

where a

nitrogen Nitrogen is the chemical element with the symbol N and atomic number 7. Nitrogen is a nonmetal and the lightest member of group 15 of the periodic table, often called the pnictogens. It is a common element in the universe, estimated at se ...

atom has replaced the

oxygen Oxygen is the chemical element with the symbol O and atomic number 8. It is a member of the chalcogen group in the periodic table, a highly reactive nonmetal, and an oxidizing agent that readily forms oxides with most elements as wel ...

atom in the ring of the structure. Iminosugars are common components of plants and may be responsible for some of their medicinal properties. The first iminosugar to be isolated from a natural source,

1-deoxynojirimycin 1-Deoxynojirimycin (DNJ or 1-DNJ), also called duvoglustat or moranolin, is an alpha-glucosidase inhibitor, most commonly found in mulberry leaves. Although it can be obtained in small quantities by brewing an herbal tea from mulberry leaves, int ...

(DNJ), found in

Mulberry ''Morus'', a genus of flowering plants in the family Moraceae, consists of diverse species of deciduous trees commonly known as mulberries, growing wild and under cultivation in many temperate world regions. Generally, the genus has 64 identif ...

, was reported in 1976, but few others were discovered until many years later. In terms of biochemical activity for medicinal applications, DNJ and 1,4-dideoxy-1,4-imino-D-arabinitol (DAB, another early example of this class of compounds) are

alpha-glucosidase inhibitor Alpha-glucosidase inhibitors (AGIs) are oral anti-diabetic drugs used for diabetes mellitus type 2 that work by preventing the digestion of carbohydrates (such as starch and table sugar). Carbohydrates are normally converted into simple sugars ( ...

s and were shown to have anti-diabetic and anti-viral activity. DNJ was modified to produce two derivatives now used as medicines, ''N''-hydroxyethyl-DNJ (

miglitol Miglitol is an oral anti-diabetic drug that acts by inhibiting the ability of the patient to break down complex carbohydrates into glucose. It is primarily used in diabetes mellitus type 2 for establishing greater glycemic control by preventing ...

) for diabetes and ''N''-butyl-DNJ (

miglustat Miglustat, sold under the brand name Zavesca, is a medication used to treat type I Gaucher disease (GD1). It is also known as N-butyldeoxynojirimycin, and is a derivative of the anti-diabetic 1-deoxynojirimycin. It was developed by Oxford GlycoSc ...

) for

Gaucher's disease Gaucher's disease or Gaucher disease () (GD) is a genetic disorder A genetic disorder is a health problem caused by one or more abnormalities in the genome. It can be caused by a mutation in a single gene (monogenic) or multiple genes (polyg ...

. Anti-cancer and anti-viral activity was subsequently observed for swainsonine—a

mannose Mannose is a sugar monomer of the aldohexose series of carbohydrates. It is a C-2 epimer of glucose. Mannose is important in human metabolism, especially in the glycosylation of certain proteins. Several congenital disorders of glycosylation ...

analogue—and

castanospermine Castanospermine is an indolizidine alkaloid first isolated from the seeds of ''Castanospermum australe''. It is a potent inhibitor of some glucosidase enzymes and has antiviral activity ''in vitro'' and in mouse models. The castanospermine deri ...

—a

glucose Glucose is a simple sugar with the molecular formula . Glucose is overall the most abundant monosaccharide, a subcategory of carbohydrates. Glucose is mainly made by plants and most algae during photosynthesis from water and carbon dioxide, using ...

analogue—in the 1980s. More than 200 have now been reported from plants and micro-organisms. Although the early compounds had biological activities due to glycosidase inhibition, an increasing number are being shown to have therapeutic potential without being glycosidase inhibitors and may interact with sugar receptors in the body or chaperone deficient enzymes such as in

lysosomal storage disorder Lysosomal storage diseases (LSDs; ) are a group of over 70 rare inherited metabolic disorders that result from defects in lysosomal function. Lysosomes are sacs of enzymes within cells that digest large molecules and pass the fragments on to other ...

s or in

cystic fibrosis Cystic fibrosis (CF) is a rare genetic disorder that affects mostly the lungs, but also the pancreas, liver, kidneys, and intestine. Long-term issues include difficulty breathing and coughing up mucus as a result of frequent lung infections. O ...

Structure and stability

The nitrogen of the iminosugar ring structure is a

hemiaminal In organic chemistry, a hemiaminal (also carbinolamine) is a functional group or type of chemical compound that has a hydroxyl group and an amine attached to the same carbon atom: . R can be hydrogen or an alkyl group. Hemiaminals are intermedia ...

linkage, which, like the

hemiacetal A hemiacetal or a hemiketal has the general formula R1R2C(OH)OR, where R1 or R2 is hydrogen or an organic substituent. They generally result from the addition of an alcohol to an aldehyde or a ketone, although the latter are sometimes called hemike ...

of a regular glycoside, is unstable. The 1-deoxy analogs of iminosugars are C-glycosides, with the nitrogen as part of an ordinary amine linkage. Their

piperidine Piperidine is an organic compound with the molecular formula (CH2)5NH. This heterocyclic compound, heterocyclic amine consists of a six-membered ring containing five methylene bridges (–CH2–) and one amine bridge (–NH–). It is a colorless ...

, pyrrolidine, or similar rings are stable.

References

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Structure and stability

See also

References