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Details

Stereochemistry ABSOLUTE
Molecular Formula C6H14N2O3.2BrH
Molecular Weight 324.011
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 2-Deoxystreptamine, dihydrobromide

SMILES

Br.Br.N[C@H]1C[C@@H](N)[C@H](O)[C@@H](O)[C@@H]1O

InChI

InChIKey=FQPOWLZRZNUTOR-SKIYRPIFSA-N
InChI=1S/C6H14N2O3.2BrH/c7-2-1-3(8)5(10)6(11)4(2)9;;/h2-6,9-11H,1,7-8H2;2*1H/t2-,3+,4+,5-,6-;;

HIDE SMILES / InChI

Molecular Formula BrH
Molecular Weight 80.912
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

PubMed

TitleDatePubMed
An efficient synthesis of mimetics of neamine for RNA recognition.
2001 May 31
Identification of L-glutamine: 2-deoxy-scyllo-inosose aminotransferase required for the biosynthesis of butirosin in Bacillus circulans.
2002 Aug
Significance of the 20-kDa subunit of heterodimeric 2-deoxy-scyllo-inosose synthase for the biosynthesis of butirosin antibiotics in Bacillus circulans.
2002 Jul
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 Jun 14
Sequence-specific recognition of the major groove of RNA by deoxystreptamine.
2002 May 21
Molecular cloning and characterization of a 2-deoxystreptamine biosynthetic gene cluster in gentamicin-producing Micromonospora echinospora ATCC15835.
2004 Aug 31
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 Feb 6
Rational design of azepane-glycoside antibiotics targeting the bacterial ribosome.
2004 Feb 9
Efficient preparation of a 1,3-diazidocyclitol as a versatile 2-deoxystreptamine precursor.
2004 Jun 25
Thermodynamics of aminoglycoside binding to aminoglycoside-3'-phosphotransferase IIIa studied by isothermal titration calorimetry.
2004 Nov 23
Discovery of non-carbohydrate inhibitors of aminoglycoside-modifying enzymes.
2005 Nov 15
Biochemical and thermodynamic characterization of compounds that bind to RNA hairpin loops: toward an understanding of selectivity.
2006 Sep 12
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 Aug 21
Medium- and short-chain dehydrogenase/reductase gene and protein families : the MDR superfamily.
2008 Dec
Heterologous production and detection of recombinant directing 2-deoxystreptamine (DOS) in the non-aminoglycoside-producing host Streptomyces venezuelae YJ003.
2008 May
The neomycin biosynthetic gene cluster of Streptomyces fradiae NCIMB 8233: genetic and biochemical evidence for the roles of two glycosyltransferases and a deacetylase.
2008 Sep 21
Aminoglycosides: molecular insights on the recognition of RNA and aminoglycoside mimics.
2009 Apr 28
Asymmetric desymmetrization of 4,5-epoxycyclohex-1-ene by enantioselective allylic oxidation.
2009 Aug 6
Revisiting plus-strand DNA synthesis in retroviruses and long terminal repeat retrotransposons: dynamics of enzyme: substrate interactions.
2009 Dec
Heterologous production of paromamine in Streptomyces lividans TK24 using kanamycin biosynthetic genes from Streptomyces kanamyceticus ATCC12853.
2009 May 31
Synthesis of neamine-derived pseudodisaccharides by stereo- and regio-selective functional group transformations.
2009 Oct 21
Development of a multicommutated flow system with chemiluminometric detection for quantification of gentamicin in pharmaceuticals.
2010
Mutation K42R in ribosomal protein S12 does not affect susceptibility of Mycobacterium smegmatis 16S rRNA A-site mutants to 2-deoxystreptamines.
2010 Aug 5
Biosynthesis of paromamine derivatives in engineered Escherichia coli by heterologous expression.
2010 May
Patents

Patents

Substance Class Chemical
Created
by admin
on Sat Dec 16 19:57:31 GMT 2023
Edited
by admin
on Sat Dec 16 19:57:31 GMT 2023
Record UNII
58G24HT23E
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
2-Deoxystreptamine, dihydrobromide
Systematic Name English
Gentamycin Impurity E
Common Name English
Streptamine, 2-deoxy-, dihydrobromide
Systematic Name English
Streptamine, hydrobromide (1:2)
Systematic Name English
Code System Code Type Description
CAS
84107-26-6
Created by admin on Sat Dec 16 19:57:31 GMT 2023 , Edited by admin on Sat Dec 16 19:57:31 GMT 2023
PRIMARY
FDA UNII
58G24HT23E
Created by admin on Sat Dec 16 19:57:31 GMT 2023 , Edited by admin on Sat Dec 16 19:57:31 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE