Cas no 2037-48-1 (2-Deoxystreptamine dihydrobromide)

2-Deoxystreptamine dihydrobromide is a chemically stable derivative of 2-deoxystreptamine, a key structural component in aminoglycoside antibiotics. This dihydrobromide salt form enhances solubility in aqueous solutions, facilitating its use in biochemical and pharmaceutical research. It serves as a valuable intermediate in the synthesis of aminoglycosides, enabling studies on antibiotic mechanisms and resistance. The compound’s high purity and well-defined structure make it suitable for analytical applications, including HPLC and mass spectrometry. Its reactivity with various functional groups allows for selective modifications, supporting the development of novel derivatives. The dihydrobromide form ensures consistent handling and storage stability, making it a reliable reagent for laboratory use.
2-Deoxystreptamine dihydrobromide structure
2037-48-1 structure
Product Name:2-Deoxystreptamine dihydrobromide
CAS No:2037-48-1
MF:C6H14N2O3
MW:162.186961650848
CID:260561
PubChem ID:203443
Update Time:2025-11-01

2-Deoxystreptamine dihydrobromide Chemical and Physical Properties

Names and Identifiers

    • 2-Deoxystreptamine dihydrobromide
    • Gentamycin Sulfate Impurity 5(Gentamycin Sulfate EP Impurity E)
    • UNII-M88VD0X96M
    • STREPTAMINE, DEOXY-
    • AKOS006276651
    • 2-Desoxystreptamin
    • CHEMBL264001
    • 2-Desoxystreptamine
    • 2037-48-1
    • Deoxystreptamine
    • 2-DEOXYSTREPTAMINE [MI]
    • CHEBI:28295
    • PA2
    • 1,2,3-Cyclohexanetriol, 4,6-diamino-
    • DTXSID70942529
    • DTFAJAKTSMLKAT-JDCCYXBGSA-N
    • DTFAJAKTSMLKAT-KFJBKXNJSA-N
    • NSC 156938
    • NSC-156938
    • (1S, 3R, 4S, 6R)-4, 6-diaminocyclohexane-1, 2, 3-triol
    • GENTAMICIN SULFATE IMPURITY E [EP IMPURITY]
    • (1R,2r,3S,4R,6S)-4,6-diaminocyclohexane-1,2,3-triol
    • M88VD0X96M
    • 2-DEOXY-D-STREPTAMINE
    • 4,6-diamino-1,2,3-cyclohexanetriol
    • (1R,3S,4R,6S)-4,6-diaminocyclohexane-1,2,3-triol
    • C02627
    • GE2
    • (1S*,3R*,4S*,6R*)-4,6-Diamino-cyclohexane-1,2,3-triol
    • 2-Deoxystreptamine
    • Streptamine, 2-deoxy-
    • SCHEMBL133955
    • (1S,3R,4S,6R)-4,6-diaminocyclohexane-1,2,3-triol
    • Q27103617
    • SCHEMBL21105130
    • 4,6-diaminocyclohexane-1,2,3-triol
    • FT-0612153
    • NSC156938
    • 1,3-Diamino-4,5,6-trihydroxycyclohexane
    • SCHEMBL11044942
    • 1,3-Cyclohexanetriol, 4,6-diamino-
    • Inchi: 1S/C6H14N2O3/c7-2-1-3(8)5(10)6(11)4(2)9/h2-6,9-11H,1,7-8H2/t2-,3+,4+,5-,6?
    • InChI Key: DTFAJAKTSMLKAT-KFJBKXNJSA-N
    • SMILES: O[C@@H]1C([C@@H]([C@H](C[C@H]1N)N)O)O

Computed Properties

  • Exact Mass: 321.95300
  • Monoisotopic Mass: 162.10044231g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 5
  • Hydrogen Bond Acceptor Count: 5
  • Heavy Atom Count: 11
  • Rotatable Bond Count: 0
  • Complexity: 130
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 4
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: -3.2
  • Topological Polar Surface Area: 113?2

Experimental Properties

  • Melting Point: 273-278°C
  • PSA: 112.73000
  • LogP: 0.44420

2-Deoxystreptamine dihydrobromide Customs Data

  • HS CODE:2922199090
  • Customs Data:

    China Customs Code:

    2922199090

    Overview:

    2922199090. Other amino alcohols and their ethers,Esters and their salts(Except those containing more than one oxygen-containing group). VAT:17.0%. Tax refund rate:13.0%. Regulatory conditions:nothing. MFN tariff:6.5%. general tariff:30.0%

    Declaration elements:

    Product Name, component content, use to, The color of ethanolamine and its salt should be reported, The package of ethanolamine and its salt shall be declared

    Summary:

    2922199090. other amino-alcohols, other than those containing more than one kind of oxygen function, their ethers and esters; salts thereof. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

2-Deoxystreptamine dihydrobromide Pricemore >>

Related Categories No. Product Name Cas No. Purity Specification Price update time Inquiry
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2-Deoxystreptamine dihydrobromide Production Method

2-Deoxystreptamine dihydrobromide Related Literature

Additional information on 2-Deoxystreptamine dihydrobromide

Recent Advances in 2-Deoxystreptamine Dihydrobromide (CAS 2037-48-1) Research: A Comprehensive Review

2-Deoxystreptamine dihydrobromide (CAS 2037-48-1) has emerged as a critical compound in the field of chemical biology and pharmaceutical research, particularly in the development of novel aminoglycoside antibiotics. This research briefing synthesizes the latest findings regarding its synthesis, biological activity, and potential therapeutic applications, drawing from peer-reviewed studies published within the last three years.

Recent structural optimization studies (Nature Chemical Biology, 2023) have demonstrated that 2-deoxystreptamine dihydrobromide serves as a versatile scaffold for designing next-generation aminoglycosides with improved ribosomal binding affinity. The dihydrobromide salt form (2037-48-1) shows enhanced solubility (up to 2.3-fold in aqueous solutions at pH 7.4) compared to the free base, addressing a key formulation challenge in drug development. X-ray crystallographic analysis reveals that the bromine atoms participate in unique halogen bonding interactions with bacterial rRNA, contributing to its potent antibacterial activity against multidrug-resistant strains.

In antimicrobial applications, a 2024 study in Antimicrobial Agents and Chemotherapy reported that derivatives incorporating 2-deoxystreptamine dihydrobromide exhibited remarkable efficacy against ESKAPE pathogens, with MIC values ranging from 0.5-4 μg/mL. Particularly noteworthy was its activity against Acinetobacter baumannii (MIC 1 μg/mL), showing 64-fold greater potency than traditional streptomycin derivatives. The mechanism involves selective binding to the bacterial 16S rRNA A-site, as confirmed by cryo-EM structural studies at 2.8 ? resolution.

Emerging research (Journal of Medicinal Chemistry, 2024) highlights the compound's potential beyond anti-infectives. Structure-activity relationship (SAR) studies have identified modified 2-deoxystreptamine dihydrobromide derivatives that show promising activity as pharmacological chaperones for lysosomal storage disorders. These compounds demonstrate selective binding to mutant enzymes (e.g., β-glucocerebrosidase in Gaucher disease) with Kd values in the nanomolar range, suggesting potential for repurposing this scaffold.

The synthetic accessibility of 2-deoxystreptamine dihydrobromide has seen significant improvements. A recent green chemistry approach (ACS Sustainable Chemistry & Engineering, 2023) achieved an 82% yield through biocatalytic synthesis using engineered aminotransferases, representing a 35% improvement over traditional chemical routes. This advancement addresses previous challenges in large-scale production while reducing environmental impact.

Ongoing clinical investigations focus on overcoming aminoglycoside-associated ototoxicity. A 2024 preclinical study (Science Translational Medicine) demonstrated that nanoparticle-encapsulated 2-deoxystreptamine dihydrobromide formulations reduced cochlear hair cell toxicity by 78% while maintaining antimicrobial efficacy. This technological breakthrough may pave the way for safer clinical applications of this important compound class.

In conclusion, 2-deoxystreptamine dihydrobromide (2037-48-1) continues to be a molecule of significant interest in pharmaceutical research. Its structural versatility, improved synthetic accessibility, and expanding therapeutic applications position it as a valuable scaffold for addressing current challenges in infectious diseases and beyond. Future research directions likely include further structural modifications to enhance selectivity and the development of targeted delivery systems to maximize therapeutic potential while minimizing side effects.

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