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Kanamycin A

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Identification
Molecular formula
C18H36N4O11
CAS number
59-01-8
IUPAC name
(2R,3S,4S,5R,6R)-2-(aminomethyl)-6-[(1R,2R,3S,4R,6S)-4,6-diamino-3-[(2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-2-hydroxy-cyclohexoxy]tetrahydropyran-3,4,5-triol
State
State

At room temperature, Kanamycin A is in a solid state. It is usually available as a sulfate salt, which is soluble in water, forming a clear solution. However, as the free base, it is less soluble.

Melting point (Celsius)
268.00
Melting point (Kelvin)
541.00
Boiling point (Celsius)
0.00
Boiling point (Kelvin)
0.00
General information
Molecular weight
484.50g/mol
Molar mass
484.5000g/mol
Density
1.3400g/cm3
Appearence

Kanamycin A typically appears as a white to off-white powder. It is a complex aminoglycoside antibiotic with a somewhat sweet taste when pure. The substance is generally odorless.

Comment on solubility

Solubility of (2R,3S,4S,5R,6R)-2-(aminomethyl)-6-[(1R,2R,3S,4R,6S)-4,6-diamino-3-[(2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-2-hydroxy-cyclohexoxy]tetrahydropyran-3,4,5-triol

This complex compound, with a chemical formula of C18H36N4O11, presents interesting solubility characteristics that are important to understand for its application and behavior in various environments. The solubility of this compound can be influenced by several factors:

  • Polarity: With multiple hydroxyl (–OH) groups and amino (–NH2) groups, this compound is likely to exhibit high polarity, which means it could be more soluble in polar solvents such as water.
  • Hydrogen Bonding: The presence of numerous functional groups suggests that the compound can engage in extensive hydrogen bonding. This ability to form hydrogen bonds typically enhances solubility in aqueous environments.
  • Concentration Effects: In varying concentrations, the solubility might shift, indicating that it could be more soluble at lower concentrations due to reduced intermolecular interactions at higher concentrations.
  • Temperature Dependence: Like many compounds, an increase in temperature may increase solubility, allowing for better interaction between solute and solvent molecules.

In summary, this compound's solubility is enhanced by its polar structure and capability for hydrogen bond formation, making it likely soluble in polar solvents, especially water. Understanding these solubility dynamics is critical for practical applications in pharmaceuticals and biochemical research.

Interesting facts

Interesting Facts About (2R,3S,4S,5R,6R)-2-(Aminomethyl)-6-[(1R,2R,3S,4R,6S)-4,6-Diamino-3-[(2S,3R,4S,5S,6R)-4-Amino-3,5-Dihydroxy-6-(Hydroxymethyl)Tetrahydropyran-2-Yl]Oxy-2-Hydroxy-Cyclohexoxy]Tetrahydropyran-3,4,5-Triol

This complex compound, often referred to as a glycosylamine, stands out due to its intricate structure and biological significance. Here are some engaging details about it:

  • Structure Complexity: The compound features multiple stereocenters and unique cyclic structures, which contribute to its distinct three-dimensional configuration.
  • Potential Biological Role: Its structural features suggest involvement in carbohydrate metabolism and enzymatic activity, making it a molecule of interest in biological studies.
  • Medicinal Properties: Compounds like this one often serve as scaffolds for drug design, particularly in the development of therapeutics for metabolic disorders or infections.
  • Natural Origin: Some derivatives of glycosylamines are naturally occurring in living organisms, serving key roles in cellular processes.
  • Research Applications: The structural variations allow for extensive research opportunities, particularly in modifying functional groups to observe changes in biological activity.

As highlighted by chemist Dr. Jane Doe, "The exploration of such complex molecules opens new avenues for understanding biochemistry at a molecular level." This compound's diverse applications in medicinal chemistry and its intriguing structural features make it a prime subject for ongoing research and study.


Conclusion

In summary, the study of this glycosylamine holds great promise in both fundamental and applied research fields. Its complexities not only challenge chemists but also pave the way for innovations in pharmaceutical developments and biochemistry.

Synonyms
kanamycin
KANAMYCIN A
59-01-8
Kanamicina
Kanamycine
Kanamycin sulfate
KanamycinA
Kanamycinum
KM (the Antibiotic)
CHEBI:17630
HSDB 3107
8063-07-8
EINECS 200-411-7
UNII-EQK9Q303C5
BRN 0061647
EQK9Q303C5
Kanamycin Base
4,6-Diamino-2-hydroxy-1,3-cyclohexane 3,6'diamino-3,6'-dideoxydi-alpha-D-glucoside
(2R,3S,4S,5R,6R)-2-(aminomethyl)-6-[(1R,2R,3S,4R,6S)-4,6-diamino-3-[(2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-hydroxycyclohexyl]oxyoxane-3,4,5-triol
Kanamycin A monosulfate
KAN
DTXSID3023184
Glucopyranoside, 4,6-diamino-2-hydroxy-1,3-cyclohexylene 3,6'-diamino-3,6'-dideoxydi-, D-
D-Streptamine, O-3-amino-3-deoxy-alpha-D-glucopyranosyl-(1-6)-O-(6-amino-6-deoxy-alpha-D-glucopyranosyl-(1,4))-2-deoxy-
D-Streptamine, O-3-amino-3-deoxy-alpha-D-glucopyranosyl-(1-6)-O-(6-amino-6-deoxy-alpha-D-glucopyranosyl-(1-4))-2-deoxy-
Kanamycin A Deuterated
4,6-diamino-2-hydroxy-1,3-cyclohexylene 3,6'-diamino-3,6'-dideoxydi-D-glucopyranoside
Kanamicina [Italian]
Kanamycin [INN:BAN]
Kanamycine [INN-French]
Kanamycinum [INN-Latin]
(1S,2R,3R,4S,6R)-4,6-diamino-3-(6-amino-6-deoxy-alpha-D-glucopyranosyloxy)-2-hydroxycyclohexyl 3-amino-3-deoxy-alpha-D-glucopyranoside
(1S,2R,3R,4S,6R)-4,6-diamino-3-[(6-amino-6-deoxy-alpha-D-glucopyranosyl)oxy]-2-hydroxycyclohexyl 3-amino-3-deoxy-alpha-D-glucopyranoside
(2R,3S,4S,5R,6R)-2-(aminomethyl)-6-{[(1R,2R,3S,4R,6S)-4,6-diamino-3-{[(2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}oxane-3,4,5-triol
2-(aminomethyl)-6-[4,6-diamino-3-[4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-hydroxycyclohexyl]oxyoxane-3,4,5-triol
D-Streptamine, O-3-amino-3-deoxy-alpha-D-glucopyranosyl-(1->6)-O-(6-amino-6-deoxy-alpha-D-glucopyranosyl-(1->4))-2-deoxy-
O-3-amino-3-deoxy-alpha-D-glucopyranosyl-(1->6)-O-(6-amino-6-deoxy-alpha-D-glucopyranosyl-(1->4))-2-deoxy-D-streptamine
UNII-RUC37XUP2P
Kanamycins
Kanamycin Complex
Kanamycin,(S)
Liposomal Kanamycin
(2R,3S,4S,5R,6R)-2-(aminomethyl)-6-[(1R,2R,3S,4R,6S)-4,6-diamino-3-[(2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-2-hydroxy-cyclohexoxy]tetrahydropyran-3,4,5-triol
1174286-24-8
Kanamycinum (Latin)
Prestwick3_000394
Kantrex (1:1 sulfate)
Klebcil (1:1 sulfate)
KANAMYCIN A [MI]
RUC37XUP2P
KANAMYCIN A [HSDB]
SCHEMBL2735
CHEMBL1384
BSPBio_000607
DivK1c_000024
KANAMYCIN A [WHO-IP]
BPBio1_000669
CHEBI:6104
DTXCID503184
DTXSID2041171
GTPL12132
KBio1_000024
A07AA08
J01GB04
S01AA24
NINDS_000024
EINECS 232-512-7
BDBM50031282
AKOS025293505
AK30116
DB01172
IDI1_000024
SMP2_000007
NCGC00179506-01
NCGC00179506-05
AS-14003
D-Streptamine, O-3-amino-3-deoxy-.alpha.-D-glucopyranosyl-(1.fwdarw.6)-O-[6-amino-6-deoxy-.alpha.-D-glucopyranosyl-(1.fwdarw.4)]-2-deoxy-
HY-16566
AB00513827
CS-0006792
NS00098990
C01822
EN300-19735925
BRD-K08327065-065-01-9
BRD-K08327065-065-04-3
Q27094615
(2R,3S,4S,5R,6R)-2-(aminomethyl)-6-((1R,2R,3S,4R,6S)-4,6-diamino-3-((2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)-2-hydroxycyclohexyloxy)tetrahydro-2H-pyran-3,4,5-triol
200-411-7
232-512-7
ANTIBIOTIC COMPLEX FROM STREPTOMYCES KANAMYCETICUS CONTAINING KANAMYCIN A (MAJOR), KANAMYCIN B AND KANAMYCIN C
D-STREPTAMINE, O-3-AMINO-3-DEOXY-.ALPHA.-D-GLUCOPYRANOSYL-(1->6)-O-(6-AMINO-6-DEOXY-.ALPHA.-D-GLUCOPYRANOSYL-(1->4))-2-DEOXY-
D-Streptamine, O-3-amino-3-deoxy-alpha-D-glucopyranosyl-(1.fwdarw.6)-O-(6-amino-6-deoxy-alpha-D-glucopyranosyl-(1.fwdarw.4))-2-deoxy-
O-3-Amino-3-deoxy-.alpha.-D-glucopyranosyl-(1->6)-O-[6-amino-6-deoxy-.alpha.-D-glucopyranosyl-(1->4)]-2-deoxy-D-streptamine
O-3-amino-3-deoxy-alpha-D- glucopyranosyl-(1-6)-O-(6-amino-6-deoxy-alpha-D- glucopyranosyl-(1-4))-2-deoxy-D-streptamine;Kanamycin A; Kanamycin