2-DEOXYSTREPTAMINE

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

Structure Search

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-

HIDE SMILES / InChI

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
An efficient synthesis of mimetics of neamine for RNA recognition.	2001 May 31	11405670
Identification of L-glutamine: 2-deoxy-scyllo-inosose aminotransferase required for the biosynthesis of butirosin in Bacillus circulans.	2002 Aug	12374384
Significance of the 20-kDa subunit of heterodimeric 2-deoxy-scyllo-inosose synthase for the biosynthesis of butirosin antibiotics in Bacillus circulans.	2002 Jul	12224638
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	12054929
Sequence-specific recognition of the major groove of RNA by deoxystreptamine.	2002 May 21	12009887
An approach for cloning biosynthetic genes of 2-deoxystreptamine-containing aminocyclitol antibiotics: isolation of a biosynthetic gene cluster of tobramycin from Streptomyces tenebrarius.	2003 Dec	14969406
Molecular cloning and characterization of a 2-deoxystreptamine biosynthetic gene cluster in gentamicin-producing Micromonospora echinospora ATCC15835.	2004 Aug 31	15359126
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	14750780
Rational design of azepane-glycoside antibiotics targeting the bacterial ribosome.	2004 Feb 9	14741274
Efficient preparation of a 1,3-diazidocyclitol as a versatile 2-deoxystreptamine precursor.	2004 Jun 25	15202904
Thermodynamics of aminoglycoside binding to aminoglycoside-3'-phosphotransferase IIIa studied by isothermal titration calorimetry.	2004 Nov 23	15544337
The neomycin biosynthetic gene cluster of Streptomyces fradiae NCIMB 8233: characterisation of an aminotransferase involved in the formation of 2-deoxystreptamine.	2005 Apr 21	15827636
Stereochemical recognition of doubly functional aminotransferase in 2-deoxystreptamine biosynthesis.	2005 Apr 27	15839685
A new family of glucose-1-phosphate/glucosamine-1-phosphate nucleotidylyltransferase in the biosynthetic pathways for antibiotics.	2005 Feb 16	15701005
Characterization of L-glutamine:2-deoxy-scyllo-inosose aminotransferase (tbmB) from Streptomyces tenebrarius.	2005 Jan 3	15582417
2-Deoxystreptamine: central scaffold of aminoglycoside antibiotics.	2005 Mar	15755076
Discovery of non-carbohydrate inhibitors of aminoglycoside-modifying enzymes.	2005 Nov 15	16140014
Size-specific ligands for RNA hairpin loops.	2005 Sep 14	16144359
Crystal structure of the bacterial ribosomal decoding site complexed with amikacin containing the gamma-amino-alpha-hydroxybutyryl (haba) group.	2006 Aug	16806634
Biochemical and thermodynamic characterization of compounds that bind to RNA hairpin loops: toward an understanding of selectivity.	2006 Sep 12	16953578
A short and scalable route to orthogonally O-protected 2-deoxystreptamine.	2007 Apr 27	17385914
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	18688488
Medium- and short-chain dehydrogenase/reductase gene and protein families : the MDR superfamily.	2008 Dec	19011751
Heterologous production and detection of recombinant directing 2-deoxystreptamine (DOS) in the non-aminoglycoside-producing host Streptomyces venezuelae YJ003.	2008 May	18633283
Improved liquid chromatographic method with pulsed electrochemical detection for the analysis of gentamicin.	2008 May 2	18199440
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	18802637
Aminoglycosides: molecular insights on the recognition of RNA and aminoglycoside mimics.	2009 Apr 28	19812740
Asymmetric desymmetrization of 4,5-epoxycyclohex-1-ene by enantioselective allylic oxidation.	2009 Aug 6	19580258
Revisiting plus-strand DNA synthesis in retroviruses and long terminal repeat retrotransposons: dynamics of enzyme: substrate interactions.	2009 Dec	21994564
Heterologous production of paromamine in Streptomyces lividans TK24 using kanamycin biosynthetic genes from Streptomyces kanamyceticus ATCC12853.	2009 May 31	19466609
Synthesis of neamine-derived pseudodisaccharides by stereo- and regio-selective functional group transformations.	2009 Oct 21	19795065
Development of a multicommutated flow system with chemiluminometric detection for quantification of gentamicin in pharmaceuticals.	2010	20981343
Mutation K42R in ribosomal protein S12 does not affect susceptibility of Mycobacterium smegmatis 16S rRNA A-site mutants to 2-deoxystreptamines.	2010 Aug 5	20700526
Biosynthetic approach for the production of new aminoglycoside derivative.	2010 Jul	20541127
Biosynthesis of paromamine derivatives in engineered Escherichia coli by heterologous expression.	2010 May	19895652
Interactions of coenzyme A with the aminoglycoside acetyltransferase (3)-IIIb and thermodynamics of a ternary system.	2010 May 18	20387904
Thermodynamics and kinetics of association of antibiotics with the aminoglycoside acetyltransferase (3)-IIIb, a resistance-causing enzyme.	2010 May 18	20387903

Patents

Substance Class	Chemical Created by `admin` on `Sat Dec 16 07:55:42 GMT 2023` Edited by `admin` on `Sat Dec 16 07:55:42 GMT 2023`
Record UNII	M88VD0X96M
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

2-DEOXYSTREPTAMINE

Common Name

English

NSC-156938

Code

English

2-DEOXY-D-STREPTAMINE

Common Name

English

STREPTAMINE, 2-DEOXY-

Common Name

English

2-DEOXYSTREPTAMINE [MI]

Common Name

English

1,2,3-CYCLOHEXANETRIOL, 4,6-DIAMINO-

Systematic Name

English

GENTAMICIN SULFATE IMPURITY E [EP IMPURITY]

Common Name

English

2-DESOXYSTREPTAMINE

Common Name

English

DEOXYSTREPTAMINE

Common Name

English

STREPTAMINE, DEOXY-

Common Name

English

Code System Code Type Description

CHEBI

72447