Valienamine

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Valienamine
Valienamine.svg
Names
Preferred IUPAC name
(1S,2S,4R,6S)-6-Amino-4-(hydroxymethyl)cyclohex-4-ene-1,2,3-triol
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
  • InChI=1S/C7H13NO4/c8-4-1-3(2-9)5(10)7(12)6(4)11/h1,4-7,9-12H,2,8H2/t4-,5+,6-,7-/m0/s1 Yes check.svgY
    Key: XPHOBMULWMGEBA-VZFHVOOUSA-N Yes check.svgY
  • InChI=1/C7H13NO4/c8-4-1-3(2-9)5(10)7(12)6(4)11/h1,4-7,9-12H,2,8H2/t4-,5+,6-,7-/m0/s1
    Key: XPHOBMULWMGEBA-VZFHVOOUBJ
  • O[C@@H]1\C(=C/[C@H](N)[C@H](O)[C@H]1O)CO
Properties
C7H13NO4
Molar mass 175.184 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Valienamine is a C-7 aminocyclitol found as a substructure of pseudooligosaccharides such as the antidiabetic drug acarbose [1] and the antibiotic validamycin. It can be found in Actinoplanes species. [2]

It is an intermediate formed by microbial degradation of validamycins. [3]

Related Research Articles

Ferrocene is an organometallic compound with the formula Fe(C5H5)2. The molecule is a complex consisting of two cyclopentadienyl rings bound to a central iron atom. It is an orange solid with a camphor-like odor, that sublimes above room temperature, and is soluble in most organic solvents. It is remarkable for its stability: it is unaffected by air, water, strong bases, and can be heated to 400 °C without decomposition. In oxidizing conditions it can reversibly react with strong acids to form the ferrocenium cation Fe(C5H5)+2.

Cytochrome P450 Class of enzymes

Cytochromes P450 (CYPs) are a superfamily of enzymes containing heme as a cofactor that functions as monooxygenases. In mammals, these proteins oxidize steroids, fatty acids, and xenobiotics, and are important for the clearance of various compounds, as well as for hormone synthesis and breakdown. In plants, these proteins are important for the biosynthesis of defensive compounds, fatty acids, and hormones.

Acarbose

Acarbose (INN) is an anti-diabetic drug used to treat diabetes mellitus type 2 and, in some countries, prediabetes. It is a generic sold in Europe and China as Glucobay, in North America as Precose, and in Canada as Prandase. It is cheap and popular in China, but not in the U.S. One physician explains the use in the U.S. is limited because it is not potent enough to justify the side effects of diarrhea and flatulence. However, a recent large study concludes "acarbose is effective, safe and well tolerated in a large cohort of Asian patients with type 2 diabetes." A possible explanation for the differing opinions is an observation that acarbose is significantly more effective in patients eating a relatively high carbohydrate Eastern diet.

Benzimidazole Chemical compound

Benzimidazole is a heterocyclic aromatic organic compound. This bicyclic compound consists of the fusion of benzene and imidazole. It is a colorless solid.

Taxane Chemical compound

Taxanes are a class of diterpenes. They were originally identified from plants of the genus Taxus (yews), and feature a taxadiene core. Paclitaxel (Taxol) and docetaxel (Taxotere) are widely used as chemotherapy agents. Cabazitaxel was FDA approved to treat hormone-refractory prostate cancer.

Alpha-glucosidase inhibitors (AGIs) are oral anti-diabetic drugs used for diabetes mellitus type 2 that work by preventing the digestion of carbohydrates. Carbohydrates are normally converted into simple sugars (monosaccharides) by alpha-glucosidase enzymes present on cells lining the intestine, enabling monosaccharides to be absorbed through the intestine. Hence, alpha-glucosidase inhibitors reduce the impact of dietary carbohydrates on blood sugar.

Calanolide A

Calanolide A is an experimental non-nucleoside reverse transcriptase inhibitor (NNRTI). This compound was extracted from the Calophyllum lanigerum, of variety austrocoriaceum, trees in Lundu, Malaysian state of Sarawak in 1992 by United States National Cancer Institute (NCI). Due to rarity of the raw materials and low yield of the active ingredient, total synthesis of the compound was devised in 1996. For the same reason, its sister compound (-)-Calanolide B have been tauted as replacement. As a result of the discovery of Calanolide A, Sarawak Medichem pharmaceuticals company was established as a joint venture between US-based MediChem Research Inc and Sarawak state government. In 2006, Craun Research, a company established by Sarawak government, acquired Sarawak MediChem. In 2016, Craun Research announced the completion of Phase I clinical trials for Calanolide A.

SLC26A8

Testis anion transporter 1 is a protein that in humans is encoded by the SLC26A8 gene.

Fluorinase

The fluorinase enzyme catalyzes the reaction between fluoride ion and the co-factor S-adenosyl-L-methionine to generate L-methionine and 5'-fluoro-5'-deoxyadenosine, the first committed product of the fluorometabolite biosynthesis pathway. The fluorinase was originally isolated from the soil bacterium Streptomyces cattleya, but homologues have since been identified in a number of other bacterial species, including Streptomyces sp. MA37, Nocardia brasiliensis and Actinoplanes sp. N902-109. This is the only known enzyme capable of catalysing the formation of a carbon-fluorine bond, the strongest single bond in organic chemistry.

The aminocyclitols are compounds related to cyclitols. They possess features of relative and absolute configuration that are characteristic of their class and have been extensively studied; but these features are not clearly displayed by general methods of stereochemical nomenclature, so that special methods of specifying their configuration are justified and have long been used. In other than stereochemical respects, their nomenclature should follow the general rules of organic chemistry.

Dynamic combinatorial chemistry

Dynamic combinatorial chemistry (DCC); also known as constitutional dynamic chemistry (CDC) is a method to the generation of new molecules formed by reversible reaction of simple building blocks under thermodynamic control. The library of these reversibly interconverting building blocks is called a dynamic combinatorial library (DCL). All constituents in a DCL are in equilibrium, and their distribution is determined by their thermodynamic stability within the DCL. The interconversion of these building blocks may involve covalent or non-covalent interactions. When a DCL is exposed to an external influence, the equilibrium shifts and those components that interact with the external influence are stabilised and amplified, allowing more of the active compound to be formed.

Cyclitol

In organic chemistry, a cyclitol is a cycloalkane containing at least three hydroxyl, each attached to a different ring carbon atom. The general formula for an unsubstituted cyclitol is C
n
H
2n-x
(OH)
x
or C
n
H
2n
O
x
where 3 ≤ xn.

Valienol Chemical compound

Valienol (streptol) is a C-7 cyclitol similar in structure to valienamine.

Pinitol Chemical compound

Pinitol is a cyclitol, a cyclic polyol. It is a known anti-diabetic agent isolated from Sutherlandia frutescens leaves. Gall plant tannins can be differentiated by their content of pinitol. It was first identified in the sugar pine. It is also found in other plants, such as in the pods of the carob tree.

Glycomimetic is a term used to refer to molecules that have structures similar to carbohydrates, but with some variation. This will normally result in modified biological properties.

Actinoplanes is a genus in the family Micromonosporaceae. They have aerial mycelia and spherical, motile spores. Actinoplanes species produce the pharmaceutically important compounds valienamine, teicoplanin, and ramoplanin.

Building block (chemistry)

Building block is a term in chemistry which is used to describe a virtual molecular fragment or a real chemical compound the molecules of which possess reactive functional groups. Building blocks are used for bottom-up modular assembly of molecular architectures: nano-particles, metal-organic frameworks, organic molecular constructs, supra-molecular complexes. Using building blocks ensures strict control of what a final compound or a (supra)molecular construct will be.

Actinoplanes utahensis is a species of bacteria and a source of the drug acarbose, an alpha-glucosidase inhibitor used in the treatment of diabetes mellitus.

1,2,3,4,5-Cyclopentanepentol Chemical compound

1,2,3,4,5-Cyclopentanepentol, also named cyclopentane-1,2,3,4,5-pentol or 1,2,3,4,5-pentahydroxycyclopentane is a chemical compound with formula C
5
H
10
O
5
or (–CHOH–)
5
, whose molecule consists of a ring of five carbon atoms, each connected to one hydrogen and one hydroxyl group. The unqualified term "cyclopentanepentol" usually refers to this compound. There are four distinct stereoisomers with this same structure.

References

  1. Laube, Heiner (March 2002). "Acarbose An Update of Its Therapeutic Use in Diabetes Treatment". Clinical Drug Investigation. 22 (3): 141–156. doi:10.2165/00044011-200222030-00001.
  2. Zhang CS, Stratmann A, Block O, et al. (June 2002). "Biosynthesis of the C(7)-cyclitol moiety of acarbose in Actinoplanes species SE50/110. 7-O-phosphorylation of the initial cyclitol precursor leads to proposal of a new biosynthetic pathway". J. Biol. Chem. 277 (25): 22853–62. doi: 10.1074/jbc.M202375200 . PMID   11937512.
  3. CID 193758 from PubChem