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Chemical Structure| 660-88-8 Chemical Structure| 660-88-8

Structure of 5-Aminovaleric acid
CAS No.: 660-88-8

Chemical Structure| 660-88-8

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5-Aminovaleric acid is believed to act as a methylene homologue of gamma-aminobutyric acid (GABA) and functions as a weak GABA agonist.

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Product Citations

Product Citations

Egleston, Matthew ; Bhat, Shridhar ; Howlader, A Hasan ; Bianchet, Mario A ; Liu, Yi ; Lopez Rovira, Laura Maria , et al.

Abstract: Sterile alpha motif histidine-aspartate domain protein 1 (SAMHD1) is an enzyme with diverse activities. Its dNTPase activity degrades all canonical dNTPs and many anticancer nucleoside drugs, while its single-stranded nucleic acid binding activity promotes DNA repair and RNA homeostasis in cells. These functions require guanine nucleotide binding to a specific allosteric site (A1) on the enzyme. We previously described how the activities of SAMHD1 could be inhibited in vitro with fragment-based inhibitor design, using dGMP as a targeting fragment for the A1 site. However, these dGMP-tethered inhibitors had poor cell permeability due to the charged guanine monophosphate group. Here, we describe a new approach where the amino form of the guanine acyclic nucleoside (NH2- ACV) is used as the targeting fragment, allowing facile coupling to activated carboxylic acids (R−COOH), either directly or using linkers. This approach generates a neutral amide instead of charged monophosphate attachment points. High-throughput screening of a ∼375 compound carboxylic acid library identified two compounds (8, 11) with similar micromolar affinities for SAMHD1. Compound 11 was obtained by direct coupling to NH2-ACV, while compound 8 used a five-carbon linker. Both inhibitors had the same dibromonaphthol component from the carboxylic acid library screen. A crystal structure of a complex between SAMHD1 and 8, combined with computational models of bound 11, suggest how the dibromonaphthol promotes binding. The findings establish that guanine-based inhibitors targeting the A1 site do not require nucleotide or cyclic nucleoside structural elements. This site targeting strategy is highly amenable to further chemical optimization.

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Product Details of 5-Aminovaleric acid

CAS No. :660-88-8
Formula : C5H11NO2
M.W : 117.15
SMILES Code : OC(=O)CCCCN
MDL No. :MFCD00008232
InChI Key :JJMDCOVWQOJGCB-UHFFFAOYSA-N
Pubchem ID :138

Safety of 5-Aminovaleric acid

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Isoform Comparison

Protocol

Bio Calculators
Preparing Stock Solutions 1mg 5mg 10mg

1 mM

5 mM

10 mM

8.54mL

1.71mL

0.85mL

42.68mL

8.54mL

4.27mL

85.36mL

17.07mL

8.54mL

Dissolving Methods
The prepared working fluid is recommended to be prepared now and used up as soon as possible in a short period of time. The percentage shown in front of the following solvent refers to the volume ratio of the solvent in the final solution; If precipitation or precipitation occurs in the preparation process, it can be assisted by heating and/or ultrasound.
Protocol 1

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