Page last updated: 2024-12-09

1,6-anhydro-beta-glucopyranose

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

## 1,6-Anhydro-β-D-glucopyranose: A Key Building Block in Research

1,6-Anhydro-β-D-glucopyranose, often simply called **1,6-anhydro-β-glucopyranose**, is a modified sugar molecule derived from glucose. It's characterized by a **cyclic ether** formed by the **linkage of the first and sixth carbon atoms** of the glucose molecule, giving it a distinctive structure.

Here's what makes this molecule significant for research:

**1. Structural Analogy:**

* 1,6-Anhydro-β-glucopyranose bears a strong resemblance to the **glucosyl unit** found in **cellulose**, a key structural component of plant cell walls. This similarity makes it a valuable tool for studying **cellulose biosynthesis and degradation**, and developing potential new bio-based materials.

**2. Synthetic Versatility:**

* The presence of the **cyclic ether** makes it a versatile building block for synthesizing various **complex carbohydrates**, including oligosaccharides and polysaccharides. These modified sugars can be used in various applications, such as:
* **Developing new drug delivery systems** based on carbohydrate conjugates.
* **Producing novel biocompatible materials** for medical implants and tissue engineering.
* **Studying carbohydrate-protein interactions** to understand cell recognition and signaling pathways.

**3. Biological Activity:**

* Research has shown that 1,6-anhydro-β-glucopyranose exhibits **biological activity**, particularly in **inhibiting certain enzymes**, like glucosidases. This property could be exploited for:
* **Developing new therapeutic agents** for treating diabetes or other metabolic disorders.
* **Studying the mechanism of action of these enzymes** and their role in various physiological processes.

**4. Chemical Reactivity:**

* The **cyclic ether** group in 1,6-anhydro-β-glucopyranose offers a **unique chemical reactivity**, allowing for various modifications and derivatizations. This opens doors for:
* **Creating new functionalized carbohydrates** with specific properties.
* **Developing new synthetic methods** for manipulating carbohydrates.
* **Exploring the potential of carbohydrates in various fields**, including catalysis, materials science, and nanotechnology.

Overall, 1,6-anhydro-β-glucopyranose is a powerful and versatile molecule with a vast potential for research. Its structural similarity to natural carbohydrates, unique chemical reactivity, and biological activity make it a valuable tool for developing new materials, therapeutic agents, and insights into fundamental biological processes.

1,6-anhydro-beta-glucopyranose: RN given refers to (beta-D)-isomer [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

levoglucosan : A anhydrohexose that is the 1,6-anhydro-derivative of beta-D-glucopyranose. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID2724705
CHEMBL ID3138649
CHEBI ID30997
SCHEMBL ID195289
MeSH IDM0063940

Synonyms (55)

Synonym
unii-5132n17fsd
5132n17fsd ,
498-07-7
nsc-46243
levoglucosan
leucoglucosan
1,6-anhydro-beta-d-glucopyranose
1,6-anhydroglucose
1,6-anhydro-beta-glucopyranose
glucosan
(1r,2s,3s,4r,5r)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triol
1,6-anhydro-beta-d-glucose
CHEBI:30997 ,
1,6-anhydro-beta-d-glucose, 99%
nsc 46243
einecs 207-855-0
ai3-61731
ccris 4273
beta-d-glucopyranose, 1,6-anhydro-
A1074
BMSE000569
AKOS006281170
(1r,2s,3s,4r,5r)-6,8-dioxa-bicyclo[3.2.1]octane-2,3,4-triol
A827859
(1r,2s,3s,4r,5r)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triol (non-preferred name)
AKOS015924837
1,6-anhydro-d-glucose
1,6-anhydro-d-glucopyranoside
GEO-00235
1,6-anhydro-b-d-glucopyranose
CHEMBL3138649
SCHEMBL195289
TWNIBLMWSKIRAT-VFUOTHLCSA-N
4pw ,
mfcd00063248
1,6-anhydro-d-glucose [usp-rs]
d-glucose, 1,6-anhydro-
1,6-anhydro-d-glucose, united states pharmacopeia (usp) reference standard
6,8-dioxabicyclo[3.2.1]octane b-delta-glucopyranose deriv.
6,8-dioxabicyclo[3.2.1]octane b-d-glucopyranose deriv.
1,6-anhydro-b-d-glucose
1,6-anhydro-beta-delta-glucopyranose
anhydro-delta-mannosan
1,6-anhydro-delta-glucose
l-glucosan
1,6-anhydro-beta-delta-glucose
1,6-anhydro--d-glucose
CS-W023160
HY-W050145
Q6535767
FS-4431
T70965
1,6-anhydro- beta -d-glucopyranose
Z1198149756
EN300-7375411
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (3)

RoleDescription
human metaboliteAny mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
biomarkerA substance used as an indicator of a biological state.
Arabidopsis thaliana metaboliteAny plant metabolite that is produced by Arabidopsis thaliana.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (1)

ClassDescription
anhydrohexoseAny anhydro sugar formally arising by elimination of water from two hydroxy groups of a single molecule of a hexose or hexose derivative.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Bioassays (3)

Assay IDTitleYearJournalArticle
AID1159550Human Phosphogluconate dehydrogenase (6PGD) Inhibitor Screening2015Nature cell biology, Nov, Volume: 17, Issue:11
6-Phosphogluconate dehydrogenase links oxidative PPP, lipogenesis and tumour growth by inhibiting LKB1-AMPK signalling.
AID977599Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM2013Molecular pharmacology, Jun, Volume: 83, Issue:6
Structure-based identification of OATP1B1/3 inhibitors.
AID977602Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM2013Molecular pharmacology, Jun, Volume: 83, Issue:6
Structure-based identification of OATP1B1/3 inhibitors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (174)

TimeframeStudies, This Drug (%)All Drugs %
pre-19903 (1.72)18.7374
1990's3 (1.72)18.2507
2000's49 (28.16)29.6817
2010's99 (56.90)24.3611
2020's20 (11.49)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 28.95

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index28.95 (24.57)
Research Supply Index5.19 (2.92)
Research Growth Index5.78 (4.65)
Search Engine Demand Index32.99 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (28.95)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials2 (1.14%)5.53%
Reviews6 (3.41%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other168 (95.45%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]