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
Biosynthesis of aminoglycoside antibiotics: cloning, expression and characterisation of an aminotransferase involved in the pathway to 2-deoxystreptamine.	2002 Dec 7	12478783
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
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 Nov	12546424
Solution chemistry of copper(II)-gentamicin complexes: relevance to metal-related aminoglycoside toxicity.	2003 Mar 10	12611506
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
Biosynthesis of 2-deoxystreptamine by three crucial enzymes in Streptomyces fradiae NBRC 12773.	2005 Dec	16506694
Crystallization and X-ray analysis of 2-deoxy-scyllo-inosose synthase, the key enzyme in the biosynthesis of 2-deoxystreptamine-containing aminoglycoside antibiotics.	2005 Jul 1	16511136
Extended sequence and functional analysis of the butirosin biosynthetic gene cluster in Bacillus circulans SANK 72073.	2005 Jun	16156513
2-Deoxystreptamine: central scaffold of aminoglycoside antibiotics.	2005 Mar	15755076
The synthesis and 16S A-site rRNA recognition of carbohydrate-free aminoglycosides.	2005 Nov 15	16168642
Crystal structure of the bacterial ribosomal decoding site complexed with amikacin containing the gamma-amino-alpha-hydroxybutyryl (haba) group.	2006 Aug	16806634
Modifications of aminoglycoside antibiotics targeting RNA.	2007 May	16892199
Medium- and short-chain dehydrogenase/reductase gene and protein families : the MDR superfamily.	2008 Dec	19011751
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
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