Homoalanosine
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Homoalanosine

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Homoalanosine is an amino acid analogue and a derivative of alanosine, an antibiotic used in the treatment of pancreatic cancer.

Category
L-Amino Acids
Catalog number
BAT-015993
CAS number
114707-36-7
Molecular Formula
C4H9N3O4
Molecular Weight
163.13
Homoalanosine
Size Price Stock Quantity
1 mg $319 In stock
IUPAC Name
(Z)-[(3S)-3-amino-3-carboxypropyl]-hydroxyimino-oxidoazanium
Appearance
Colorless Powder
Purity
98%
Density
1.7±0.1 g/cm3
Melting Point
181-183°C
Boiling Point
385.1±52.0 °C at 760 mmHg
Solubility
Soluble in Water
InChI
InChI=1S/C4H9N3O4/c5-3(4(8)9)1-2-7(11)6-10/h3,10H,1-2,5H2,(H,8,9)/b7-6-/t3-/m0/s1
InChI Key
RMTXCTHJOJRMCZ-LDHNOCAXSA-N
Canonical SMILES
C(C[N+](=NO)[O-])C(C(=O)O)N

Homoalanosine, a novel amino acid derivative, has garnered significant attention for its diverse applications in various scientific and industrial fields. One of its key applications is in the area of pharmaceuticals. Homoalanosine is utilized as a chiral building block in the synthesis of complex drug molecules. Its unique structural properties facilitate the creation of drugs with enhanced efficacy and reduced side effects. Moreover, homoalanosine’s ability to improve the stability and bioavailability of pharmaceutical compounds makes it a valuable component in drug development and production.

In the field of biotechnology, homoalanosine has found application as a precursor in the synthesis of novel biomolecules. Enzyme engineering, for instance, benefits from homoalanosine’s versatile chemistry. By incorporating homoalanosine into enzyme structures, researchers can manipulate enzyme activity and stability, leading to the creation of more efficient catalysts for industrial processes. Additionally, homoalanosine’s role in protein engineering helps in the design of proteins with enhanced functionalities, which are crucial for various biotechnological applications, such as biosensors and diagnostic tools.

Agriculture also benefits from the application of homoalanosine. As a novel amino acid derivative, it plays a pivotal role in the development of advanced agrochemicals, including herbicides and pesticides. Homoalanosine-based compounds are designed to target specific biochemical pathways in weeds and pests, thereby providing a more targeted and environmentally friendly approach to crop protection. Furthermore, the use of homoalanosine in plant metabolic engineering helps in enhancing the nutritional profile of crops, thereby contributing to food security and sustainable agricultural practices.

The industrial manufacturing sector leverages homoalanosine in the production of high-performance materials. Its incorporation in polymer synthesis results in the creation of materials with superior mechanical properties, such as increased tensile strength and elasticity. These enhanced materials are crucial in various applications, including automotive, aerospace, and consumer electronics industries. Additionally, homoalanosine’s role in developing biodegradable polymers aligns with the growing demand for sustainable and eco-friendly materials, helping to reduce environmental impact and promote circular economy practices.

1. Studies on a new herbicidal antibiotic, homoalanosine
S Fushimi, S Nishikawa, N Mito, M Ikemoto, M Sasaki, H Seto J Antibiot (Tokyo). 1989 Sep;42(9):1370-8. doi: 10.7164/antibiotics.42.1370.
Homoalanosine having a herbicidal activity was isolated from the culture filtrate of a soil isolate SC-1688 which was classified as Streptomyces galilaeus. The chemical structure of homoalanosine was determined to be L-2-amino-4-nitrosohydroxyaminobutyric acid by analyses of spectral and biological data. The antibiotic has high herbicidal activity at low concentrations against especially common cocklebur and ladysthumb among the tested weeds and crops. Foliar application of this antibiotic inhibited the growth of roots and buds. This result indicated that homoalanosine had a systemic herbicidal activity.
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