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D-Alaninol

* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.

A reagent used in the synthesis of naphthyridinone integrase inhibitors.

Category

Amino Alcohol

Catalog number

BAT-000367

CAS number

35320-23-1

Molecular Formula

C3H9NO

Molecular Weight

75.10

IUPAC Name

(2R)-2-aminopropan-1-ol

Synonyms

(R)-(-)-2-Amino-1-propanol; (2R)-2-aminopropan-1-ol

Appearance

Colorless to light yellow liquid

Purity

> 95 % by HPLC

Density

0.965 g/mL

Melting Point

8 °C

Boiling Point

173-176 °C (lit.)

Storage

Store at -20 °C

Solubility

Soluble in Water

InChI

InChI=1S/C3H9NO/c1-3(4)2-5/h3,5H,2,4H2,1H3/t3-/m1/s1

InChI Key

BKMMTJMQCTUHRP-GSVOUGTGSA-N

Canonical SMILES

CC(CO)N

D-Alaninol, a versatile chiral amino alcohol, finds significant applications in the pharmaceutical and chemical industries. Here are the key applications of D-Alaninol presented with high perplexity and burstiness:

Chiral Synthesis: Positioned as a pivotal chiral building block in pharmaceutical synthesis, D-Alaninol plays a crucial role in crafting enantiomerically pure pharmaceuticals. Its inherent chirality enables the meticulous production of compounds with precise stereochemistry a critical factor for the efficacy and safety of numerous drugs. This attribute renders D-Alaninol indispensable in the pharmaceutical realm particularly in shaping medications for intricate conditions such as cardiovascular diseases and central nervous system disorders.

Asymmetric Catalysis: Stepping into the realm of asymmetric catalysis, D-Alaninol emerges as a catalytic powerhouse functioning either as a chiral ligand or auxiliary. This catalytic prowess aids in orchestrating reactions that yield chiral molecules with exceptional selectivity and efficiency. The asymmetric reactions catalyzed by D-Alaninol stand at the forefront of producing active pharmaceutical ingredients and fine chemicals marking it as a cornerstone in the chemical synthesis domain.

Chemical Intermediates: Within the realm of chemical manufacturing, D-Alaninol assumes a critical role as a prime intermediate in generating diverse essential compounds. Its functional groups equip it to engage in a myriad of chemical reactions forming intermediates that eventually metamorphose into valuable end products. This adaptability proves instrumental in the synthesis of agrochemicals fragrances and other specialty chemicals showcasing D-Alaninol's contribution to the chemical industry's versatility.

Research and Development: Embracing academia and industry alike D-Alaninol serves as a key protagonist in exploring novel chemical reactions and product formulations. Scientists leverage D-Alaninol as a model compound to delve into the chiral influences on reaction mechanisms and product distributions. This research endeavor holds the potential to unveil fresh applications and innovative utilities of D-Alaninol across various sectors promising advancements in chemical innovation and discovery.

1. A New Anisotropic Charge-Equilibration Method for Self-Assembly of Organics on Metal Surface: d-Alaninol on Cu(100)

A Palma, M Satta J Chem Theory Comput. 2016 Aug 9;12(8):4042-51. doi: 10.1021/acs.jctc.6b00430. Epub 2016 Jul 25.

The supramolecular chemistry at surfaces has been extensively studied by quantum and classical computational models in order to simulate and reproduce the correct energetics and structures of adsorbed molecules on surfaces at various coverages. We have developed a classical tool able to sample the configuration space overcoming the topological constraints of the standard classical molecular dynamics. Our model is based on the charge equilibration procedure combined with an anisotropic pairwise atomic interaction where an angular dependence, with respect to the metal surface, is explicitly taken into account. The d-alaninol molecule has been chosen as a prototype of a flexible and multifunctional chemical compound which can form manifold complex configurations upon absorption on a metal surface. A detailed analysis of molecular structures and energetics of partial and full coverage has been carried out. The experimental STM image of the monolayer is correctly reproduced by our calculations, indicating that this new approach represents a step forward in the efficient simulation of complex molecular self-assembly.

2. Discovery and in vivo effects of novel human natriuretic peptide receptor A (NPR-A) agonists with improved activity for rat NPR-A

Takehiko Iwaki, Taisaku Tanaka, Kazuo Miyazaki, Yamato Suzuki, Yoshihiko Okamura, Akira Yamaki, Makoto Iwanami, Naomi Morozumi, Mayumi Furuya, Yoshiaki Oyama Bioorg Med Chem. 2017 Dec 15;25(24):6680-6694. doi: 10.1016/j.bmc.2017.11.006. Epub 2017 Nov 6.

Natriuretic peptide receptor A (NPR-A) agonists were evaluated in vivo by optimizing the structure of quinazoline derivatives to improve agonistic activity for rat NPR-A. A 1,4-Cis-aminocyclohexylurea moiety at 4-position and hydroxy group of d-alaninol at 2-position on the quinazoline ring were found to be important factors in improving rat NPR-A activity. We identified potent quinazoline and pyrido[2,3-d]pyrimidine derivatives against rat NPR-A, with double-digit nanomolar EC50 values. The in vivo results showed that compound 56b administered at 1.0 mg/kg/min significantly increased plasma cGMP concentration and urine volume in rats. We discovered novel potent NPR-A agonists that showed agonistic effects similar to those of atrial natriuretic peptide.

3. [Phylogenetic diversity characteristics of soil bacteria producing nematode-attracting volatiles and identification of their active compounds]

Yu'e Hao, Guiping Mou, Aitao He, Jiaqin Xi, Faxiang Yang, Minghe Mo Wei Sheng Wu Xue Bao. 2011 Nov 4;51(11):1454-60.

Objective: This study characterized the phylogenetic diversity of soil bacteria producing nematode-attracting volatiles and their nematode-attracting compounds. Results would enhance our understanding on the interaction between nematodes and soil microorganisms and potentially enhance the biocontrol efficiency when combined the attractants with nemacides. Methods: Bacteria producing volatiles with functions of nematode-attracting activities were isolated from 187 agricultural soil samples collected in 26 provinces of China with the method of double-Petri dishes. The phylogenetic diversity of these bacteria was characterized by RFLP-16S rRNA gene sequence analysis. The nematode-attracting volatiles of bacteria were detected using the SPME-GC/MS, and volatile compounds with attractive activity were determined by confirming with individual commercial compounds. Results: Among the 3800 bacteria isolated from the 187 soil samples, 196 isolates(5.16% of the total) showed attractive activity (AN)more than 30% to Panagrellus redivivus. Of the 196 isolates, 66 (1.74%) showed AN > or = 70%, 62 isolates (1.63%) showed AN between 50% and 70%, and 68 isolates (1.79%) showed AN less than 50%. Phylogenetic analysis revealed that the 196 bacteria were clustered into 5 groups: Bacilli, Gammaproteobacteria, Alphaproteobacteria, Sphingobacteria and Actinobacteria. But, Bacillus were the dominant, which covered 13 species. And 11 volatiles with nematode-attracting activity were determined, including benzaldehyde, 2-heptanone, benzyl benzoate, ethyl palmitate, (+)-longifolene, benzyl alcohol, p-anisaldehyde, vanatone, ethyl butyrate, isovanilin and d-alaninol. Conclusion: Some species of bacteria in agriculture soil can produce volatiles to attract nematodes.