Name: 3-Azido-D-alanine hydrochloride
Brand: BOC Sciences
Price: -- USD
Availability: MadeToOrder

Synonyms

3-Azido-D-alanine HCl; beta-Azido-D-2,3-diaminopropionic acid hydrochloride; H-D-DAP(N3)-OH HCl

IUPAC Name

(2R)-2-amino-3-azidopropanoic acid;hydrochloride

Canonical SMILES

C(C(C(=O)O)N)N=[N+]=[N-].Cl

InChI

InChI=1S/C3H6N4O2.ClH/c4-2(3(8)9)1-6-7-5;/h2H,1,4H2,(H,8,9);1H/t2-;/m1./s1

InChIKey

MQDWRZHPCDDSJZ-HSHFZTNMSA-N

Storage

Store at 2-8 °C

3-Azido-D-alanine hydrochloride, a versatile compound with diverse applications in biochemical and biotechnological fields, occupies a pivotal role in various high-perplexity and high-burstiness scenarios. Here, we delve into four key applications that exemplify these characteristics with a blend of perplexity and burstiness:

Proteomics: Integrating 3-Azido-D-alanine hydrochloride into live cell proteins propels scientists into the realm of bioorthogonal chemistry, revolutionizing the exploration of protein synthesis and modifications. This strategic incorporation enables precise tagging and tracking of proteins within complex biological systems using cutting-edge click chemistry methods. Unveiling protein interactions and functions at a molecular level offers profound insights into the intricacies of cellular processes, unraveling the mysteries of biological pathways.

Peptide Synthesis: In the domain of synthetic biology, 3-Azido-D-alanine hydrochloride serves as a crucial amino acid analog for constructing peptide chains with elevated perplexity. This strategic utilization introduces azide groups into peptides, facilitating further functionalization through intricate click chemistry reactions. Such modifications play a pivotal role in advancing biomaterials, pharmaceuticals, and diagnostic tools, epitomizing the innovative capacity of this compound in pushing the boundaries of biomolecular engineering.

Cell Surface Engineering: Leveraging 3-Azido-D-alanine hydrochloride for cell surface modifications via metabolic labeling signifies a paradigm shift in biotechnological research, injecting a burst of complexity into the field. Through the intricate introduction of azide groups into cellular components, researchers pave the way for bioconjugation with various tags or probes, intensifying the burstiness in studying complex cell surface dynamics, receptor-ligand interactions, and cellular communication. This avant-garde approach opens up novel pathways for exploring the nuances of cellular behavior and function, enriching our understanding of cell surface phenomena.

Immunology: Spearheading vaccine development, 3-Azido-D-alanine hydrochloride assumes a critical role in generating modified antigens to enhance immune responses with heightened perplexity. Incorporating azide groups into antigenic proteins facilitates the creation of well-defined conjugates with adjuvants or delivery systems, underscoring the complexity and diversity of immunological investigations. This innovative strategy aims to bolster the efficacy of vaccines against a myriad of diseases, showcasing the transformative potential of this compound in the realm of immunotherapy, charting a new course in the fight against infectious pathogens.

1. Synthesis, analgesic and anti-inflammatory activities evaluation of some bi-, tri- and tetracyclic condensed pyrimidines

Kamilia M Amin, Mona M Hanna, Hanan E Abo-Youssef, Riham F George Eur J Med Chem. 2009 Nov;44(11):4572-84. doi: 10.1016/j.ejmech.2009.06.028. Epub 2009 Jul 1.

Novel series of bicyclic pyrrolo[1,2-c]pyrimidines 3a-g, 5, 6a, b, and 7a, b, tricyclic pyrimido[5,4-e]pyrrolo[1,2-c]pyrimidines 8a-c, 9a-g, 13a-c, 17, 18a, b, 19, 20a,b and 21 and tetracyclic condensed pyrimidines 14, 22 and 23 were synthesized through different chemical reactions. Structures of all synthesized pyrimidine derivatives were supported by spectral and elemental analyses. Analgesic activity evaluation was carried out using acetic acid-induced writhing assay, and all compounds exerted comparable activity to indomethacin. The anti-inflammatory activity evaluation was performed using carrageenan-induced paw edema in rats, the potency of the bicyclic derivatives 3a-f and 7b revealed comparable activity to indomethacin without gastric ulceration. The tricyclic derivatives 13a and 20a exerted good activity, however, they induced gastric ulcers while 13b and 13c showed moderate activity without ulceration. In case of tetracyclic derivatives, compound 14 exhibited the highest potency and safety profile.

2. One pot synthesis of pyrimidine and bispyrimidine derivatives and their evaluation for anti-inflammatory and analgesic activities

Sham M Sondhi, Shubhi Jain, Monica Dinodia, Rakesh Shukla, Ram Raghubir Bioorg Med Chem. 2007 May 15;15(10):3334-44. doi: 10.1016/j.bmc.2007.03.028. Epub 2007 Mar 13.

A number of pyrimidine derivatives (1-10) have been synthesized by condensation of 4-isothiocyanato-4-methylpentan-2-one with furfurylamine, histamine, 1-(3-aminopropyl)imidazole, 1-(3-aminopropyl)-2-pyrrolidinone, 2-aminobenzonitrile and 3-isothiocyanatobutanal with 1-(3-aminopropyl)-2-pyrrolidinone and 2-hydrazinopyridine under different reaction conditions. Various bispyrimidine derivatives (11-15) were obtained by condensation of 4-isothiocyanato-4-methylpentan-2-one with 2,4,8,10-tetraoxaspiro[5,5]undecane3,9-dipropamine (11'), 1,4-bis(3-aminopropyl)piperazine (13'), 3,5-diamino 1,2,4-triazole (15') and 3-isothiocyanatobutanal with 2,4,8,10-tetraoxaspiro[5,5]undecane 3,9-dipropamine, 1,4-bis(3-aminopropyl)piperazine. All these compounds were characterized by correct FT-IR, (1)H NMR, MS and elemental analysis. These compounds were screened for anti-inflammatory and analgesic activities. Anti-inflammatory activity of 3 is comparable while analgesic activity was found to be better than that of standard drug.

3. Synthesis, anti-inflammatory and analgesic activity evaluation of some amidine and hydrazone derivatives

Sham M Sondhi, Monica Dinodia, Ashok Kumar Bioorg Med Chem. 2006 Jul 1;14(13):4657-63. doi: 10.1016/j.bmc.2006.02.014. Epub 2006 Feb 28.

A number of amidine derivatives (3a-i) were synthesized by condensation of cyanopyridine and cyanopyrazine with sulfonylhydrazides in the presence of sodium methoxide. 2-Acetylpyridine and 4-acetylpyridine were condensed with sulfonylhydrazides by microwave irradiation in solid phase to give corresponding hydrazones (5a-d). Indole-3-carboxaldehyde was condensed with sulfonylhydrazides by refluxing in acetic acid to give corresponding condensation product (5e and f). All the compounds, that is, 3a-i and 5a-f were purified by crystallization or by column chromatography. Structures of all the synthesized compounds are supported by correct IR, (1)H NMR, mass spectral and analytical data. Anti-inflammatory activity evaluation was carried out using carrageenin-induced paw oedema assay and compounds 3e,f and 5e exhibited good anti-inflammatory activity, that is 52%, 37% and 38% at 50 mg/kg po, respectively. Analgesic activity evaluation was carried out using acetic acid writhing assay and compounds 3a,c,e and 5f showed good analgesic activity, that is, 50%, 50%, 50% and 60% at 50 mg/kg po, respectively.

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