Home Aminos (2R,3S,4R,5R,6R)-5-Amino-2-(aminomethyl)-6-(((1R,2R,3S,4R,6S)-4,6-diamino-2,3-dihydroxycyclohexyl)oxy)tetrahydro-2H-pyran-3,4-diol

(2R,3S,4R,5R,6R)-5-Amino-2-(aminomethyl)-6-(((1R,2R,3S,4R,6S)-4,6-diamino-2,3-dihydroxycyclohexyl)oxy)tetrahydro-2H-pyran-3,4-diol

CAS No.:
3947-65-7
Catalog Number:
AG00BXGX
Molecular Formula:
Molecular Weight:
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
1mg
98%(HPLC)
In Stock USA
United States
$155
- +
5mg
98%(HPLC)
In Stock USA
United States
$344
- +
10mg
98%(HPLC)
In Stock USA
United States
$643
- +
Product Description
Catalog Number:
AG00BXGX
Chemical Name:
(2R,3S,4R,5R,6R)-5-Amino-2-(aminomethyl)-6-(((1R,2R,3S,4R,6S)-4,6-diamino-2,3-dihydroxycyclohexyl)oxy)tetrahydro-2H-pyran-3,4-diol
CAS Number:
3947-65-7
MDL Number:
MFCD00023857
IUPAC Name:
(2R,3S,4R,5R,6R)-5-amino-2-(aminomethyl)-6-[(1R,2R,3S,4R,6S)-4,6-diamino-2,3-dihydroxycyclohexyl]oxyoxane-3,4-diol
InChI:
InChI=1S/C12H26N4O6/c13-2-5-8(18)9(19)6(16)12(21-5)22-11-4(15)1-3(14)7(17)10(11)20/h3-12,17-20H,1-2,13-16H2/t3-,4+,5-,6-,7+,8-,9-,10-,11-,12-/m1/s1
InChI Key:
SYJXFKPQNSDJLI-HKEUSBCWSA-N
UNII:
5981U00LY0
Properties
Complexity:
378  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
10  
Defined Bond Stereocenter Count:
0
Exact Mass:
322.185g/mol
Formal Charge:
0
Heavy Atom Count:
22  
Hydrogen Bond Acceptor Count:
10  
Hydrogen Bond Donor Count:
8  
Isotope Atom Count:
0
Molecular Weight:
322.362g/mol
Monoisotopic Mass:
322.185g/mol
Rotatable Bond Count:
3  
Topological Polar Surface Area:
204A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
-5.4  
Literature
Title Journal
Efficient stabilization of phosphodiester (PO), phosphorothioate (PS), and 2'-O-methoxy (2'-OMe) DNA·RNA hybrid duplexes by amino sugars. Biochemistry 20120710
Synthesis and antibacterial activity of novel neamine derivatives: preponderant role of the substituent position on the neamine core. Organic & biomolecular chemistry 20120628
Discovery of parallel pathways of kanamycin biosynthesis allows antibiotic manipulation. Nature chemical biology 20111009
Conjugate of neamine and 2-deoxystreptamine mimic connected by an amide bond. Bioorganic & medicinal chemistry letters 20110815
Understanding the origins of bacterial resistance to aminoglycosides through molecular dynamics mutational study of the ribosomal A-site. PLoS computational biology 20110701
The Pseudomonas aeruginosa membranes: a target for a new amphiphilic aminoglycoside derivative? Biochimica et biophysica acta 20110601
Influence of charge and structure on the coordination chemistry of copper aminoglycosides. Dalton transactions (Cambridge, England : 2003) 20110227
Identification of ligands for the Tau exon 10 splicing regulatory element RNA by using dynamic combinatorial chemistry. Chemistry (Weinheim an der Bergstrasse, Germany) 20110207
Biosynthesis of ribostamycin derivatives by reconstitution and heterologous expression of required gene sets. Applied biochemistry and biotechnology 20110201
NMR and amber analysis of the neamine pharmacophore for the design of novel aminoglycoside antibiotics. Bioorganic chemistry 20110201
Rational design and synthesis of potent aminoglycoside antibiotics against resistant bacterial strains. Bioorganic & medicinal chemistry 20110101
Neamine inhibits cell proliferation, migration, and invasion in H7402 human hepatoma cells. Saudi medical journal 20101201
Aminoglycoside binding to Oxytricha nova telomeric DNA. Biochemistry 20101116
Antibacterial activities of aminoglycoside antibiotics-derived cationic amphiphiles. Polyol-modified neomycin B-, kanamycin A-, amikacin-, and neamine-based amphiphiles with potent broad spectrum antibacterial activity. Journal of medicinal chemistry 20100513
Two-dimensional combinatorial screening of a bacterial rRNA A-site-like motif library: defining privileged asymmetric internal loops that bind aminoglycosides. Biochemistry 20100309
The nebramycin aminoglycoside profiles of Streptomyces tenebrarius and their characterization using an integrated liquid chromatography-electrospray ionization-tandem mass spectrometric analysis. Analytica chimica acta 20100219
Synthesis of novel aminoglycosides via allylic azide rearrangement for investigating the significance of 2'-amino group. Bioorganic & medicinal chemistry 20100215
Synthesis and antimicrobial evaluation of amphiphilic neamine derivatives. Journal of medicinal chemistry 20100114
Mutation K42R in ribosomal protein S12 does not affect susceptibility of Mycobacterium smegmatis 16S rRNA A-site mutants to 2-deoxystreptamines. PloS one 20100101
Synthesis and transfection properties of a series of lipidic neamine derivatives. Bioconjugate chemistry 20091101
Synthesis of neamine-derived pseudodisaccharides by stereo- and regio-selective functional group transformations. Organic & biomolecular chemistry 20091021
Enantioseparation by MEKC using a ligand exchange-based chiral pseudostationary phase. Electrophoresis 20090801
Synthesis and evaluation of novel neamine derivatives effectively targeting to RNA. Bioorganic & medicinal chemistry letters 20090415
Neamine inhibits prostate cancer growth by suppressing angiogenin-mediated rRNA transcription. Clinical cancer research : an official journal of the American Association for Cancer Research 20090315
Search for novel aminoglycosides by combining fragment-based virtual screening and 3D-QSAR scoring. Journal of chemical information and modeling 20090201
Chiral ligand-exchange chromatography of amino acids using porous graphitic carbon coated with a dinaphthyl derivative of neamine. Analytical and bioanalytical chemistry 20090101
Synthesis of a phosphonate-linked aminoglycoside-coenzyme a bisubstrate and use in mechanistic studies of an enzyme involved in aminoglycoside resistance. Chemistry (Weinheim an der Bergstrasse, Germany) 20090101
Aminoglycosides: molecular insights on the recognition of RNA and aminoglycoside mimics. Perspectives in medicinal chemistry 20090101
Two-dimensional combinatorial screening identifies specific 6'-acylated kanamycin A- and 6'-acylated neamine-RNA hairpin interactions. Biochemistry 20081202
Studies on the synthesis of neamine-dinucleosides and neamine-PNA conjugates and their interaction with RNA. Bioorganic & medicinal chemistry letters 20081015
Two-dimensional combinatorial screening identifies specific aminoglycoside-RNA internal loop partners. Journal of the American Chemical Society 20080820
Identification of tobramycin impurities for quality control process monitoring using high-performance anion-exchange chromatography with integrated pulsed amperometric detection. Journal of pharmaceutical and biomedical analysis 20080805
Copper(II) complexes of lipophilic aminoglycoside derivatives for the amino acid enantiomeric separation by ligand-exchange liquid chromatography. Journal of chromatography. A 20080328
Biosynthesis of 3'-deoxy-carbamoylkanamycin C in a Streptomyces tenebrarius mutant strain by tacB gene disruption. The Journal of antibiotics 20080201
Fluorescence correlation spectroscopy at single molecule level on the Tat-TAR complex and its inhibitors. Biopolymers 20080101
Structure-function relationship of novel X4 HIV-1 entry inhibitors - L- and D-arginine peptide-aminoglycoside conjugates. The FEBS journal 20071201
Synthesis of a neamine dimer targeting the dimerization initiation site of HIV-1 RNA. Organic letters 20071025
Design and synthesis of a structurally constrained aminoglycoside. The Journal of organic chemistry 20070706
Unique O-ribosylation in the biosynthesis of butirosin. Bioorganic & medicinal chemistry 20070701
Monitoring aminoglycoside-induced conformational changes in 16S rRNA through acrylamide quenching. Bioorganic & medicinal chemistry 20070601
Aminoglycoside antibiotic derivatives: preparation and evaluation of toxicity on cochlea and vestibular tissues and antimicrobial activity. Bioorganic & medicinal chemistry 20070601
Fluorescent HIV-1 Dimerization Initiation Site: design, properties, and use for ligand discovery. Journal of the American Chemical Society 20070321
Elaboration of neosamine rings in the biosynthesis of neomycin and butirosin. Chembiochem : a European journal of chemical biology 20070212
Determination of neomycin sulfate and impurities using high-performance anion-exchange chromatography with integrated pulsed amperometric detection. Journal of pharmaceutical and biomedical analysis 20070104
Mechanism of RNA cleavage catalyzed by sequence specific polyamide nucleic acid-neamine conjugate. Oligonucleotides 20070101
Nucleobase modified neamines, their synthesis and binding specificity for HIV TAR RNA. Nucleic acids symposium series (2004) 20070101
Synthesis and antibacterial activity of novel neamine derivatives. Bioorganic & medicinal chemistry letters 20061215
Selectively guanidinylated derivatives of neamine. Syntheses and inhibition of anthrax lethal factor protease. Bioorganic & medicinal chemistry letters 20061001
Binding of aminoglycosidic antibiotics to the oligonucleotide A-site model and 30S ribosomal subunit: Poisson-Boltzmann model, thermal denaturation, and fluorescence studies. Journal of medicinal chemistry 20060907
A molecular dynamics simulation study of an aminoglycoside/A-site RNA complex: conformational and hydration patterns. Biochimie 20060801
Mixed-type noncompetitive inhibition of anthrax lethal factor protease by aminoglycosides. The FEBS journal 20060701
Neamine derivatives having a nucleobase with a lysine or an arginine as a linker, their synthesis and evaluation as potential inhibitors for HIV TAR-Tat. Bioorganic & medicinal chemistry 20060415
Determination of tobramycin and impurities using high-performance anion exchange chromatography with integrated pulsed amperometric detection. Journal of pharmaceutical and biomedical analysis 20060303
Interactions of designer antibiotics and the bacterial ribosomal aminoacyl-tRNA site. Chemistry & biology 20060201
Cationic polyamines inhibit anthrax lethal factor protease. BMC pharmacology 20060101
Neamine inhibits xenografic human tumor growth and angiogenesis in athymic mice. Clinical cancer research : an official journal of the American Association for Cancer Research 20051215
The synthesis and 16S A-site rRNA recognition of carbohydrate-free aminoglycosides. Bioorganic & medicinal chemistry letters 20051115
Neamine dimers targeting the HIV-1 TAR RNA. Bioorganic & medicinal chemistry letters 20051101
The RNA-bound conformation of neamine as determined by transferred NOE experiments. Chembiochem : a European journal of chemical biology 20050701
Structure-activity relationships of bivalent aminoglycosides and evaluation of their microbiological activities. Bioorganic & medicinal chemistry letters 20050415
Structure-activity relationships of aminoglycoside-arginine conjugates that bind HIV-1 RNAs as determined by fluorescence and NMR spectroscopy. FEBS letters 20041119
Chemoenzymatic synthesis and high-throughput screening of an aminoglycoside-polyamine library: identification of high-affinity displacers and DNA-binding ligands. Journal of the American Chemical Society 20041006
A peptide nucleic acid-neamine conjugate that targets and cleaves HIV-1 TAR RNA inhibits viral replication. Journal of medicinal chemistry 20040923
Disaccharide mimetics of the aminoglycoside antibiotic neamine. Chembiochem : a European journal of chemical biology 20040906
Voltage-dependent inhibition of rat skeletal muscle sodium channels by aminoglycoside antibiotics. Pflugers Archiv : European journal of physiology 20040501
Fluorinated aminoglycosides and their mechanistic implication for aminoglycoside 3'-phosphotransferases from Gram-negative bacteria. Biochemistry 20040309
Regioselective glycosylation of neamine core: a facile entry to kanamycin B related analogues. Organic letters 20040219
Structure-activity relationship of neomycin, paromomycin, and neamine-arginine conjugates, targeting HIV-1 gp120-CXCR4 binding step. Antiviral research 20031101
Crystal structure of geneticin bound to a bacterial 16S ribosomal RNA A site oligonucleotide. Journal of molecular biology 20030227
Crystal structure of a complex between the aminoglycoside tobramycin and an oligonucleotide containing the ribosomal decoding a site. Chemistry & biology 20020601
Design of novel antibiotics that bind to the ribosomal acyltransfer site. Journal of the American Chemical Society 20020403
An efficient synthesis of mimetics of neamine for RNA recognition. Organic letters 20010531
Study of aminoglycoside-nucleic acid interactions by an HPLC method. Bioorganic & medicinal chemistry letters 20010423
Aminoglycoside antibiotics, neamine and its derivatives as potent inhibitors for the RNA-protein interactions derived from HIV-1 activators. Bioorganic & medicinal chemistry letters 20010226
Which aminoglycoside ring is most important for binding? A hydropathic analysis of gentamicin, paromomycin, and analogues. Bioorganic & medicinal chemistry letters 20010122
Synthesis of biomimetic analogs of neomycin B: potential inhibitors of the HIV RNA Rev response element. Nucleosides, nucleotides & nucleic acids 20000101
Small molecules that selectively block RNA binding of HIV-1 Rev protein inhibit Rev function and viral production. Cell 19930924
Screening for new compounds with antiherpes activity. Antiviral research 19841001
Properties