L-Arabinose
[CAS# 5328-37-0]

Identification

• Classification: Biochemical >> Carbohydrate >> Monosaccharide
• Name: L-Arabinose
• Synonyms: (+)-Arabinose; L-(+)-Arabinose; NSC 1941
• Molecular Formula: C₅H₁₀O₅
• Molecular Weight: 150.13
• CAS Registry Number: 5328-37-0
• EC Number: 226-214-6
• SMILES: C([C@@H]([C@@H]([C@H](C=O)O)O)O)O

Properties

• Melting point: 155 ºC
• alpha: 104 º (c=6, in water 23 ºC)

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H332-H335
• Precautionary Statements: P261-P280-P305+P351+P338

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2A	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315

Discovory and Applicatios

L-arabinose is a naturally occurring sugar and an important member of the pentose family that was first discovered and isolated from gum arabic in the early 19th century. Its unique structure, characterized by a five-carbon skeleton, attracted the interest of chemists exploring carbohydrate chemistry. This discovery marked the beginning of extensive research on its properties and potential applications.

In biological sciences, L-arabinose is an essential component for studying microbial genetics and metabolic pathways. It has been implicated in the utilization of arabinose by bacteria, such as Escherichia coli, to activate specific gene expression pathways. This property makes L-arabinose a valuable tool in genetic engineering and synthetic biology, helping to control the expression of recombinant proteins and manipulate microbial behavior.

In addition to its biological role, L-arabinose has practical applications in various industrial fields. It is a precursor for synthetic drug intermediates and helps in the production of antiviral agents and nucleoside analogs. Its inclusion in cosmetic formulations highlights its potential as a natural ingredient with moisturizing and skin conditioning benefits.

L-arabinose's status as a natural sugar substitute has attracted attention from the nutritional science community. It has a low glycemic index and is suitable for dietary interventions to control blood sugar levels. As a non-caloric sweetener, it offers a viable alternative to traditional sugars, catering to consumers seeking healthier dietary options.

Advances in biotechnology have expanded the use of L-arabinose in enzyme production and biofuel synthesis. Enzymatic processes utilizing L-arabinose have been optimized to efficiently produce high-value products such as specialty chemicals and biodegradable polymers. Its role in sustainable bioprocessing is consistent with global initiatives to promote renewable resources and reduce environmental impact.

Looking ahead, ongoing research will continue to explore new applications and improve L-arabinose production methods. Advances in metabolic engineering and biocatalysis are expected to increase its efficiency and expand its application. As technology evolves, L-arabinose remains at the forefront of innovation, driving discoveries that impact industry and scientific disciplines.

References

1970. Chemical Composition of the Cell Wall of the H37Ra Strain of Mycobacterium tuberculosis. Journal of Bacteriology, 102(3).
DOI: 10.1128/jb.102.3.733-739.1970

2024. A bacterial platform for producing aromatic esters from glycerol. Nature Chemical Engineering.
DOI: 10.1038/s44286-024-00148-9

1979. Xylose, Arabinose, and Rhamnose Fermentation by Bacteroides ruminicola. Applied and Environmental Microbiology, 38(1).
DOI: 10.1128/aem.38.1.7-12.1979