Trehalosamine

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Trehalosamine
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • 2:InChI=1S/C12H23NO10/c13-5-8(18)6(16)3(1-14)21-11(5)23-12-10(20)9(19)7(17)4(2-15)22-12/h3-12,14-20H,1-2,13H2/t3-,4-,5-,6-,7-,8-,9+,10-,11-,12-/m1/s1
    Key: YSVQUZOHQULZQP-OCEKCAHXSA-N
  • 3:InChI=1S/C12H23NO10/c13-5-6(16)3(1-14)21-11(8(5)18)23-12-10(20)9(19)7(17)4(2-15)22-12/h3-12,14-20H,1-2,13H2/t3-,4-,5+,6-,7-,8-,9+,10-,11-,12-/m1/s1
    Key: OHNBYBTUSOVUMK-PNKJYEMWSA-N
  • 4:InChI=1S/C12H23NO10/c13-5-3(1-14)21-11(9(19)7(5)17)23-12-10(20)8(18)6(16)4(2-15)22-12/h3-12,14-20H,1-2,13H2/t3-,4-,5-,6-,7+,8+,9-,10-,11-,12-/m1/s1
    Key: GXKCUFUYTFWGNK-LIZSDCNHSA-N
  • 6:InChI=1S/C12H23NO10/c13-1-3-5(15)7(17)9(19)11(21-3)23-12-10(20)8(18)6(16)4(2-14)22-12/h3-12,14-20H,1-2,13H2/t3-,4-,5-,6-,7+,8+,9-,10-,11-,12-/m1/s1
    Key: JMUYOTNYEBNHGG-LIZSDCNHSA-N
  • 2:C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O[C@@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)N)O)O)O
  • 3:C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O[C@@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)O)N)O)O
  • 4:C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O[C@@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)O)O)N)O
  • 6:C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O[C@@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CN)O)O)O)O)O)O)O
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Trehalosamines are amino sugars in which a hydroxyl group of trehalose is replaced with an amino group. While 2-, 3-, and 4-trehalosamine derived from actinomycetes have been reported as natural compounds, [1] [2] [3] 6-trehalosamine has been reported as a synthetic compound. [4] They have weak antimicrobial activity [1] [2] [3] [5] and could be considered as a class of aminoglycoside antibiotics. The properties and functions of 4-trehalosamine have been well investigated as follows. [6]

Contents

Protective activity

As "a trehalose possessing an amino group", trehalosamine shares many properties and characteristics in common with trehalose; in addition, unique functions due to the presence of an amino group are also suggested. Trehalose is used as a protective agent for starch, protein, cells, or tissues due to its non-reducing sugar moiety having lower non-specific reactivity than reducing sugars and high moisturizing and protective activities. [7] In many cases, 4-trehalosamine exhibits these protective activities either comparable to or marginally higher than those of trehalose. In addition, 4-trehalosamine exhibits a strong pH buffering activity near neutrality, while trehalose does not have such ability. Therefore, it is expected to be added to foods and industrial products as a trehalose-type moisturizing and protective agent with pH buffering ability. [6]

Effects on living organisms

Trehalose is known to exhibit autophagy-inducing activity, anti-inflammatory activity, molecular chaperone activity, or antioxidant activity in a broad sense in vivo. [8] It is being studied for use as a treatment for neurodegenerative diseases and lifestyle-related diseases, as a medication, supplement, or as a prebiotic. However, as it is hydrolyzed in the body by trehalase, a trehalose-degrading enzyme, its physiological effect is limited. There is also concern that blood glucose levels may rise due to the generation of glucose as the degradation product. But, 4-trehalosamine is not degraded by human trehalase, and it has been confirmed in experiments with mice that it is non-toxic and does not raise blood sugar levels. For this reason, 4-trehalosamine is also attracting attention as a substitute for trehalose in these applications. [6]

As a starting material for synthesis of trehalose derivatives

Generally, saccharides have multiple hydroxyl groups in the molecule, and to systematically synthesize specific derivatives, complicated protocols such as repeated protection and deprotection are required. Although it is limited to the amino group site, various derivatives can be synthesized relatively easily by utilizing the reactivity different from that of the hydroxyl group of trehalosamine. Low-molecular-weight derivatives such as azide, surfactant IMCTA-C14, fluorescent or biotin-labeled derivatives have been developed so far, and application to the development of polymeric compounds containing periodic trehalose structures is also expected. [6] [9]

Related Research Articles

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In chemistry, a hexose is a monosaccharide (simple sugar) with six carbon atoms. The chemical formula for all hexoses is C6H12O6, and their molecular weight is 180.156 g/mol.

<span class="mw-page-title-main">Neomycin</span> Type of antibiotic

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<span class="mw-page-title-main">Gentamicin</span> Antibiotic medication

Gentamicin is an aminoglycoside antibiotic used to treat several types of bacterial infections. This may include bone infections, endocarditis, pelvic inflammatory disease, meningitis, pneumonia, urinary tract infections, and sepsis among others. It is not effective for gonorrhea or chlamydia infections. It can be given intravenously, by intramuscular injection, or topically. Topical formulations may be used in burns or for infections of the outside of the eye. It is often only used for two days until bacterial cultures determine what specific antibiotics the infection is sensitive to. The dose required should be monitored by blood testing.

<span class="mw-page-title-main">Amino sugar</span>

In organic chemistry, an amino sugar is a sugar molecule in which a hydroxyl group has been replaced with an amine group. More than 60 amino sugars are known, with one of the most abundant being N-acetyl-D-glucosamine, which is the main component of chitin.

<span class="mw-page-title-main">Aminoglycoside</span> Antibacterial drug

Aminoglycoside is a medicinal and bacteriologic category of traditional Gram-negative antibacterial medications that inhibit protein synthesis and contain as a portion of the molecule an amino-modified glycoside (sugar). The term can also refer more generally to any organic molecule that contains amino sugar substructures. Aminoglycoside antibiotics display bactericidal activity against Gram-negative aerobes and some anaerobic bacilli where resistance has not yet arisen but generally not against Gram-positive and anaerobic Gram-negative bacteria.

<span class="mw-page-title-main">Trehalose</span> Chemical compound

Trehalose is a sugar consisting of two molecules of glucose. It is also known as mycose or tremalose. Some bacteria, fungi, plants and invertebrate animals synthesize it as a source of energy, and to survive freezing and lack of water.

<span class="mw-page-title-main">Trehalase</span> Class of enzymes

The enzyme Trehalase is a glycoside hydrolase, produced by cells in the brush border of the small intestine, which catalyzes the conversion of trehalose to glucose. It is found in most animals.

<span class="mw-page-title-main">Novobiocin</span> Chemical compound

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<span class="mw-page-title-main">Bafilomycin</span> Chemical compound

The bafilomycins are a family of macrolide antibiotics produced from a variety of Streptomycetes. Their chemical structure is defined by a 16-membered lactone ring scaffold. Bafilomycins exhibit a wide range of biological activity, including anti-tumor, anti-parasitic, immunosuppressant and anti-fungal activity. The most used bafilomycin is bafilomycin A1, a potent inhibitor of cellular autophagy. Bafilomycins have also been found to act as ionophores, transporting potassium K+ across biological membranes and leading to mitochondrial damage and cell death.

<span class="mw-page-title-main">Spectinomycin</span> Antibiotic

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<span class="mw-page-title-main">Neocarzinostatin</span> Chemical compound

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<span class="mw-page-title-main">Oleandomycin</span> Chemical compound

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<span class="mw-page-title-main">Desosamine</span> Chemical compound

Desosamine is a 3-(dimethylamino)-3,4,6-trideoxyhexose found in certain macrolide antibiotics such as the commonly prescribed erythromycin, azithromycin, clarithroymcin, methymycin, narbomycin, oleandomycin, picromycin and roxithromycin. As the name suggests, these macrolide antibiotics contain a macrolide or lactone ring and they are attached to the ring Desosamine which is crucial for bactericidal activity. The biological action of the desosamine-based macrolide antibiotics is to inhibit the bacterial ribosomal protein synthesis. These antibiotics which contain Desosamine are widely used to cure bacterial-causing infections in human respiratory system, skin, muscle tissues, and urethra.

<span class="mw-page-title-main">Ribostamycin</span> Aminoglycoside antibiotic

Ribostamycin is an aminoglycoside-aminocyclitol antibiotic isolated from a streptomycete, Streptomyces ribosidificus, originally identified in a soil sample from Tsu City of Mie Prefecture in Japan. It is made up of 3 ring subunits: 2-deoxystreptamine (DOS), neosamine C, and ribose. Ribostamycin, along with other aminoglycosides with the DOS subunit, is an important broad-spectrum antibiotic with important use against human immunodeficiency virus and is considered a critically important antimicrobial by the World Health Organization., Resistance against aminoglycoside antibiotics, such as ribostamycin, is a growing concern. The resistant bacteria contain enzymes that modify the structure through phosphorylation, adenylation, and acetylation and prevent the antibiotic from being able to interact with the bacterial ribosomal RNAs.

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.

<span class="mw-page-title-main">Pikromycin</span> Chemical compound

Pikromycin was studied by Brokmann and Hekel in 1951 and was the first antibiotic macrolide to be isolated. Pikromycin is synthesized through a type I polyketide synthase system in Streptomyces venezuelae, a species of Gram-positive bacterium in the genus Streptomyces. Pikromycin is derived from narbonolide, a 14-membered ring macrolide. Along with the narbonolide backbone, pikromycin includes a desosamine sugar and a hydroxyl group. Although Pikromycin is not a clinically useful antibiotic, it can be used as a raw material to synthesize antibiotic ketolide compounds such as ertythromycins and new epothilones.

<span class="mw-page-title-main">Antipain</span> Chemical compound

Antipain is an oligopeptide that is isolated from actinomycetes and used in biochemical research as a protease inhibitor of trypsin and papain. It was discovered in 1972 and was the first natural peptide found that contained an ureylene group. Antipain can aid in prevention of coagulation in blood. It is an inhibitor of serine and cysteine proteases.

2-deoxy-scyllo-Inosose synthase is an enzyme with systematic name D-glucose-6-phosphate phosphate-lyase (2-deoxy-scyllo-inosose-forming). This enzyme catalyses the following chemical reaction

Streptomyces isolates have yielded the majority of human, animal, and agricultural antibiotics, as well as a number of fundamental chemotherapy medicines. Streptomyces is the largest antibiotic-producing genus of Actinomycetota, producing chemotherapy, antibacterial, antifungal, antiparasitic drugs, and immunosuppressants. Streptomyces isolates are typically initiated with the aerial hyphal formation from the mycelium.

<span class="mw-page-title-main">C-1027</span> Chemical compound

C-1027 or lidamycin is an antitumor antibiotic consisting of a complex of an enediyne chromophore and an apoprotein. It shows antibiotic activity against most Gram-positive bacteria. It is one of the most potent cytotoxic molecules known, due to its induction of a higher ratio of DNA double-strand breaks than single-strand breaks.

References

  1. 1 2 Arcamone F, Bizioli F (1957). "Isolation and constitution of trehalosamine, a new aminosugar from a streptomyces". Gazz. Chim. Ital. 87: 896–902.
  2. 1 2 Naganawa H, Usui N, Takita T, Hamada M, Maeda K (February 1974). "Letter: 4-Amino-4-deoxy-alpha, alpha-trehalose, a new metabolite of a Streptomyces". The Journal of Antibiotics. 27 (2): 145–146. doi: 10.7164/antibiotics.27.145 . PMID   4826088.
  3. 1 2 Dolak LA, Castle TM, Laborde AL (July 1980). "3-Trehalosamine, a new disaccharide antibiotic". The Journal of Antibiotics. 33 (7): 690–694. doi: 10.7164/antibiotics.33.690 . PMID   6773914.
  4. ↑ Hanessian S, Lavallee P (November 1972). "Synthesis of 6-amino-6-deoxy-α,α-trehalose: a positional isomer of trehalosamine". The Journal of Antibiotics. 25 (11): 683–684. doi: 10.7164/antibiotics.25.683 . PMID   4647840.
  5. ↑ Groenevelt JM, Meints LM, Stothard AI, Poston AW, Fiolek TJ, Finocchietti DH, et al. (August 2018). "Chemoenzymatic Synthesis of Trehalosamine, an Aminoglycoside Antibiotic and Precursor to Mycobacterial Imaging Probes". The Journal of Organic Chemistry. 83 (15): 8662–8667. doi:10.1021/acs.joc.8b00810. PMC   6358420 . PMID   29973045.
  6. 1 2 3 4 Wada SI, Arimura H, Nagayoshi M, Sawa R, Kubota Y, Matoba K, et al. (June 2022). "Rediscovery of 4-Trehalosamine as a Biologically Stable, Mass-Producible, and Chemically Modifiable Trehalose Analog". Advanced Biology. 6 (6): e2101309. doi: 10.1002/adbi.202101309 . PMID   35297567. S2CID   247499479.
  7. ↑ Higashiyama T (January 2002). "Novel functions and applications of trehalose". Pure and Applied Chemistry. 74 (7): 1263–1269. doi: 10.1351/pac200274071263 . ISSN   1365-3075. S2CID   28311022.
  8. ↑ Menzies FM, Fleming A, Rubinsztein DC (June 2015). "Compromised autophagy and neurodegenerative diseases". Nature Reviews. Neuroscience. 16 (6): 345–357. doi:10.1038/nrn3961. PMID   25991442. S2CID   19272817.
  9. ↑ Teramoto N, Sachinvala ND, Shibata M (August 2008). "Trehalose and trehalose-based polymers for environmentally benign, biocompatible and bioactive materials". Molecules. 13 (8): 1773–1816. doi: 10.3390/molecules13081773 . PMC   6245314 . PMID   18794785.
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