Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C6H14N2O3 |
| Molecular Weight | 162.187 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 5 / 5 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
N[C@H]1C[C@@H](N)[C@H](O)[C@@H](O)[C@@H]1O
InChI
InChIKey=DTFAJAKTSMLKAT-JDCCYXBGSA-N
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-
| Molecular Formula | C6H14N2O3 |
| Molecular Weight | 162.187 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 5 / 5 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Mutation K42R in ribosomal protein S12 does not affect susceptibility of Mycobacterium smegmatis 16S rRNA A-site mutants to 2-deoxystreptamines. | 2010-08-05 |
|
| Biosynthetic approach for the production of new aminoglycoside derivative. | 2010-07 |
|
| Interactions of coenzyme A with the aminoglycoside acetyltransferase (3)-IIIb and thermodynamics of a ternary system. | 2010-05-18 |
|
| Thermodynamics and kinetics of association of antibiotics with the aminoglycoside acetyltransferase (3)-IIIb, a resistance-causing enzyme. | 2010-05-18 |
|
| Biosynthesis of paromamine derivatives in engineered Escherichia coli by heterologous expression. | 2010-05 |
|
| Development of a multicommutated flow system with chemiluminometric detection for quantification of gentamicin in pharmaceuticals. | 2010 |
|
| Revisiting plus-strand DNA synthesis in retroviruses and long terminal repeat retrotransposons: dynamics of enzyme: substrate interactions. | 2009-12 |
|
| Synthesis of neamine-derived pseudodisaccharides by stereo- and regio-selective functional group transformations. | 2009-10-21 |
|
| Asymmetric desymmetrization of 4,5-epoxycyclohex-1-ene by enantioselective allylic oxidation. | 2009-08-06 |
|
| Heterologous production of paromamine in Streptomyces lividans TK24 using kanamycin biosynthetic genes from Streptomyces kanamyceticus ATCC12853. | 2009-05-31 |
|
| Aminoglycosides: molecular insights on the recognition of RNA and aminoglycoside mimics. | 2009-04-28 |
|
| Medium- and short-chain dehydrogenase/reductase gene and protein families : the MDR superfamily. | 2008-12 |
|
| The neomycin biosynthetic gene cluster of Streptomyces fradiae NCIMB 8233: genetic and biochemical evidence for the roles of two glycosyltransferases and a deacetylase. | 2008-09-21 |
|
| Mechanistic study on the reaction of a radical SAM dehydrogenase BtrN by electron paramagnetic resonance spectroscopy. | 2008-08-26 |
|
| A convenient synthesis of orthogonally protected 2-deoxystreptamine (2-DOS) as an aminocyclitol scaffold for the development of novel aminoglycoside antibiotic derivatives against bacterial resistance. | 2008-08-21 |
|
| Fully orthogonally protected 2-deoxystreptamine from kanamycin. | 2008-07-04 |
|
| Improved liquid chromatographic method with pulsed electrochemical detection for the analysis of gentamicin. | 2008-05-02 |
|
| Heterologous production and detection of recombinant directing 2-deoxystreptamine (DOS) in the non-aminoglycoside-producing host Streptomyces venezuelae YJ003. | 2008-05 |
|
| Characterization and mechanistic study of a radical SAM dehydrogenase in the biosynthesis of butirosin. | 2007-12-12 |
|
| Aminoglycoside antibiotic derivatives: preparation and evaluation of toxicity on cochlea and vestibular tissues and antimicrobial activity. | 2007-06-01 |
|
| Modifications of aminoglycoside antibiotics targeting RNA. | 2007-05 |
|
| A short and scalable route to orthogonally O-protected 2-deoxystreptamine. | 2007-04-27 |
|
| Biochemical and thermodynamic characterization of compounds that bind to RNA hairpin loops: toward an understanding of selectivity. | 2006-09-12 |
|
| Crystal structure of the bacterial ribosomal decoding site complexed with amikacin containing the gamma-amino-alpha-hydroxybutyryl (haba) group. | 2006-08 |
|
| Biosynthesis of 2-deoxystreptamine by three crucial enzymes in Streptomyces fradiae NBRC 12773. | 2005-12 |
|
| The synthesis and 16S A-site rRNA recognition of carbohydrate-free aminoglycosides. | 2005-11-15 |
|
| Discovery of non-carbohydrate inhibitors of aminoglycoside-modifying enzymes. | 2005-11-15 |
|
| Size-specific ligands for RNA hairpin loops. | 2005-09-14 |
|
| Synthesis of a library of stereo- and regiochemically diverse aminoglycoside derivatives. | 2005-08-07 |
|
| Crystallization and X-ray analysis of 2-deoxy-scyllo-inosose synthase, the key enzyme in the biosynthesis of 2-deoxystreptamine-containing aminoglycoside antibiotics. | 2005-07-01 |
|
| Extended sequence and functional analysis of the butirosin biosynthetic gene cluster in Bacillus circulans SANK 72073. | 2005-06 |
|
| Stereochemical recognition of doubly functional aminotransferase in 2-deoxystreptamine biosynthesis. | 2005-04-27 |
|
| The neomycin biosynthetic gene cluster of Streptomyces fradiae NCIMB 8233: characterisation of an aminotransferase involved in the formation of 2-deoxystreptamine. | 2005-04-21 |
|
| 2-Deoxystreptamine: central scaffold of aminoglycoside antibiotics. | 2005-03 |
|
| A new family of glucose-1-phosphate/glucosamine-1-phosphate nucleotidylyltransferase in the biosynthetic pathways for antibiotics. | 2005-02-16 |
|
| Characterization of L-glutamine:2-deoxy-scyllo-inosose aminotransferase (tbmB) from Streptomyces tenebrarius. | 2005-01-03 |
|
| Thermodynamics of aminoglycoside binding to aminoglycoside-3'-phosphotransferase IIIa studied by isothermal titration calorimetry. | 2004-11-23 |
|
| Molecular cloning and characterization of a 2-deoxystreptamine biosynthetic gene cluster in gentamicin-producing Micromonospora echinospora ATCC15835. | 2004-08-31 |
|
| Efficient preparation of a 1,3-diazidocyclitol as a versatile 2-deoxystreptamine precursor. | 2004-06-25 |
|
| Rational design of azepane-glycoside antibiotics targeting the bacterial ribosome. | 2004-02-09 |
|
| Active site mapping of 2-deoxy-scyllo-inosose synthase, the key starter enzyme for the biosynthesis of 2-deoxystreptamine. Mechanism-based inhibition and identification of lysine-141 as the entrapped nucleophile. | 2004-02-06 |
|
| An approach for cloning biosynthetic genes of 2-deoxystreptamine-containing aminocyclitol antibiotics: isolation of a biosynthetic gene cluster of tobramycin from Streptomyces tenebrarius. | 2003-12 |
|
| Novel acyclic deoxystreptamine mimetics targeting the ribosomal decoding site. | 2003-09-05 |
|
| Solution chemistry of copper(II)-gentamicin complexes: relevance to metal-related aminoglycoside toxicity. | 2003-03-10 |
|
| Biosynthesis of aminoglycoside antibiotics: cloning, expression and characterisation of an aminotransferase involved in the pathway to 2-deoxystreptamine. | 2002-12-07 |
|
| First identification of Streptomyces genes involved in the biosynthesis of 2-deoxystreptamine-containing aminoglycoside antibiotics--genetic and evolutionary analysis of L-glutamine:2-deoxy-scyllo-inosose aminotransferase genes. | 2002-11 |
|
| Identification of L-glutamine: 2-deoxy-scyllo-inosose aminotransferase required for the biosynthesis of butirosin in Bacillus circulans. | 2002-08 |
|
| Significance of the 20-kDa subunit of heterodimeric 2-deoxy-scyllo-inosose synthase for the biosynthesis of butirosin antibiotics in Bacillus circulans. | 2002-07 |
|
| Importance of specific hydrogen-bond donor-acceptor interactions for the key carbocycle-forming reaction catalyzed by 2-deoxy-scyllo-inosose synthase in the biosynthesis of 2-deoxystreptamine-containing aminocyclitol antibiotics. | 2002-06-14 |
|
| Sequence-specific recognition of the major groove of RNA by deoxystreptamine. | 2002-05-21 |
Patents
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 21:46:13 GMT 2025
by
admin
on
Mon Mar 31 21:46:13 GMT 2025
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| Record UNII |
M88VD0X96M
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| Record Status |
Validated (UNII)
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65069
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m4180
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DTXSID70942529
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M88VD0X96M
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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