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Deoxyadenosine

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Identification
Molecular formula
C10H13N5O3
CAS number
951-78-0
IUPAC name
(2R,3R,4S,5R)-2-[6-(hydroxyamino)purin-9-yl]-5-(hydroxymethyl)tetrahydrofuran-3,4-diol
State
State

At room temperature, deoxyadenosine is in a solid crystalline state, typical of nucleosides, which are stable and non-reactive under standard laboratory conditions.

Melting point (Celsius)
228.00
Melting point (Kelvin)
501.15
Boiling point (Celsius)
420.00
Boiling point (Kelvin)
693.15
General information
Molecular weight
251.24g/mol
Molar mass
251.2410g/mol
Density
2.2300g/cm3
Appearence

Deoxyadenosine is a white crystalline powder that is generally odorless. Its appearance is typical of many nucleoside structures, with a crystalline nature that can vary slightly in size depending on the preparation method used.

Comment on solubility

Solubility of (2R,3R,4S,5R)-2-[6-(hydroxyamino)purin-9-yl]-5-(hydroxymethyl)tetrahydrofuran-3,4-diol

The solubility of complex organic compounds, such as (2R,3R,4S,5R)-2-[6-(hydroxyamino)purin-9-yl]-5-(hydroxymethyl)tetrahydrofuran-3,4-diol, is influenced by several key factors. When assessing its solubility, we can consider the following aspects:

  • Polarity: The presence of multiple functional groups, such as hydroxyl (-OH) and amino (–NH2), generally increases the compound's polarity, enhancing its ability to dissolve in polar solvents like water.
  • Hydrogen bonding: The functional groups can engage in hydrogen bonding with solvent molecules, which significantly boosts solubility in polar environments.
  • Molecular interactions: The structure may allow for specific interactions with other molecules, further impacting solubility; for example, interactions with ions or solutes present in a solution.

As quoted by chemists, "Like dissolves like." This principle highlights the importance of the solvent's nature in determining solubility. Given the hydrophilic characteristics of this compound, it is likely to be more soluble in aqueous solutions than in organic solvents. Therefore:

  • Do not hesitate to conduct experimental solubility tests in various solvents to fully characterize the solubility profile.
  • Consider the environmental conditions, such as temperature and pH, which can further influence solubility outcomes.

In summary, the solubility of (2R,3R,4S,5R)-2-[6-(hydroxyamino)purin-9-yl]-5-(hydroxymethyl)tetrahydrofuran-3,4-diol is expected to be relatively high in polar solvents due to its functional groups, yet precise data can only be obtained through experimental investigation.

Interesting facts

Interesting Facts about (2R,3R,4S,5R)-2-[6-(hydroxyamino)purin-9-yl]-5-(hydroxymethyl)tetrahydrofuran-3,4-diol

This compound, often referred to in scientific literature for its significance in biochemistry, showcases a fascinating structural complexity that is pivotal in the realm of nucleic acids and related biochemistry pathways. Here are some interesting points:

  • Role in Nucleotide Metabolism: This compound is closely related to nucleotides, which are the building blocks of DNA and RNA. It plays a key role in the synthesis and regulation of these essential biomolecules.
  • Hydroxyamino Group: The presence of a hydroxyamino group in its structure is significant for its chemical reactivity and functionality, often participating in various biochemical reactions.
  • Chirality: The chirality indicated by its stereochemical configuration (2R, 3R, 4S, 5R) highlights its potential as an enantiomerically pure compound, which can lead to differing biological activity compared to its indistinguishable counterparts, underscoring the importance of molecular orientation in biological systems.
  • Importance in Research: Compounds like this one are crucial in pharmaceutical research, often serving as potential inhibitors or modulators in enzyme-catalyzed processes. They may also provide insights into disease mechanisms at the molecular level.
  • Structure-Activity Relationship (SAR): The detailed structure of this molecule allows for extensive research into SAR, helping scientists to understand how changes in the molecular structure can influence biological activity.

“Understanding such compounds not only enhances our knowledge of molecular biology but also paves the way for innovative therapeutic approaches.”

This compound is a perfect example of how intricate molecular designs can lead to substantial implications in the biochemical world, reinforcing the intricate connection between chemistry and biology.

Synonyms
Inosine oxime
6-N-Hydroxyadenosine
6-Hydroxyadenosine
HO-N-Adenosine
6-N-Hydroxylaminopurine riboside
N(sup 6)-Hydroxyadenosine
6-Hydroxylaminopurine riboside
CCRIS 2559
NSC 529410
UNII-QR2S87K5XC
EINECS 222-306-5
N(sup 6)-Hydroxylaminopurine riboside
BRN 0568198
6-Hydroxyamino-9-beta-D-ribofuranosylpurine
INOSINE, 6-OXIME
N6-HYDROXYLADENOSINE
NSC-529410
ADENINE, N-HYDROXY-9-RIBOFURANOSYL-
6-hydroxylamino-9-beta-d-ribofuranosylpurine
6-N-HYDROXYAMINO-9-.BETA.-D-RIBOFURANOSYLPURINE
6-(HYDROXYLAMINO)-9-.BETA.-D-RIBOFURANOSYLPURINE
9-.BETA.-D-RIBOFURANOSYL-6-(HYDROXYLAMINO)PURINE
6-(HYDROXYLAMINO)-9-BETA-D-RIBOFURANOSYLPURINE
6-N-HYDROXYAMINO-9-BETA-D-RIBOFURANOSYLPURINE
9-BETA-D-RIBOFURANOSYL-6-(HYDROXYLAMINO)PURINE
N-Hydroxyadenosine
N6-Hydroxyadenosine
Adenosine, N-hydroxy-
6-Hydroxyaminopurine riboside
N6-Hydroxylaminopurine riboside
6-Hydroxyaminopurine ribonucleoside
3414-62-8
QR2S87K5XC
(2R,3R,4S,5R)-2-[6-(hydroxyamino)purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol
CHEMBL236537
SCHEMBL3500846
QROZCFCNYCVEDO-KQYNXXCUSA-N
DTXSID701023373
AKOS040749992
HY-118793
CS-0068557
Q27287458
(2R,3R,4S,5R)-2-[6-(hydroxyamino)purin-9-yl]-5-(hydroxymethyl)tetrahydrofuran-3,4-diol