Amino acid hydroxamates glycine hydroxamate

• CAS: 5349-80-4
• Catalog Number: ACM5349804
• Category: Main Products
• Molecular Weight: 90.08
• Molecular Formula: C₂H₆N₂O₂
• Synonyms: 2-AMINO-N-HYDROXY-ACETAMIDE;AMINO ACID HYDROXAMATES GLYCINE HYDROXAMATE;GLYCINE HYDROXAMATE;GLYCINE HYDROXAMIC ACID;acetamide, 2-amino-N-hydroxy-;1-Hydroxy-2-aminoethanone oxime;2-Aminoacetohydroximic acid;Aminoacetohydroxamic acid
• IUPAC Name: 2-amino-N-hydroxyacetamide
• SMILES: C(C(=O)NO)N
• InChI Key: VDBCTDQYMZSQFQ-UHFFFAOYSA-N
• Boiling Point: 441.7ºC at 760 mmHg
• Melting Point: 131°C
• Flash Point: 176.9ºC
• Density: 1.094g/cm³
• Exact Mass: 90.04290

Case Study

Glycine Hydroxamate as a Candidate Tyrosinase Inhibitor and Anti-Melanogenic Agent for Cosmetics

Lin, Yin-Shiou, et al. Amino acids 47.3 (2015): 617-625.

A panel of hydroxamic-acid analogues of amino acids was selected for initial screening due to effects on melanogenesis, as tyrosinase (Cu-containing enzyme) and its regulatory network (MITF → TYR/TRP expression) are the most important components in pigment production. Glycine hydroxamate (GH) was of particular interest because hydroxamates are known to alter protonation behavior and chelate metal ions, properties that can affect enzyme interaction and cellular signaling.
GH was found to be the most effective inhibitor of mushroom tyrosinase out of eight amino-acid hydroxamates in this study, and reduced melanin synthesis in B16F10 melanoma cells stimulated with α-MSH or IBMX. GH is a noncompetitive inhibitor of tyrosinase monophenolase activity (l-tyrosine substrate), and also decreased tyrosinase protein and related melanogenic markers (TRP-1, TRP-2, MITF), lowered intracellular cAMP and the downstream CREB/phospho-CREB, and produced anti-melanogenic effects comparable to arbutin at lower mass concentrations, supporting further development of GH as a cosmetic hypopigmentation ingredient.

Glycine Hydroxamate as a Versatile Ligand for Water-Soluble 15-MC-5 Cu(II)-Ln(III) Metallamacrocycles

Katkova, M. A. Russian Journal of Coordination Chemistry 44.4 (2018): 284-300.

Amino-hydroxamic acids such as glycine hydroxamate (GlyHA) present multiple O/N donor atoms in a compact scaffold that readily chelates transition-metal ions and templates multinuclear assemblies; their water solubility and multidentate binding make them attractive building blocks for metallamacrocycles (metallacrowns) with central lanthanide sites that can be further functionalized via axial ligation for imaging or materials applications.
In this work, GlyHA serves as an effective, water-compatible ligand for assembling polynuclear 15-MC-5 metallamacrocycles that incorporate five Cu(II) centers and a central lanthanide (Ln3+). Simple, room-temperature one-pot reactions in water (mixing lanthanide salt, copper acetate and GlyHA) produce dark-blue, water-soluble Cu-Ln metallamacrocyles with well defined ring architectures and tunable apical coordination.
Representative europium complexes demonstrate either a largely planar 15-membered ring with nitrate/water apical ligands or a distorted, bowl-shaped ring with a bidentate acetate axial ligand (Eu-O average distances: ~2.381 Å for nitrate-coordinated Eu; ~2.492 Å for acetate-coordinated Eu). These GlyHA-based metallamacrocyles have been explored as potential NMR contrast agents and, for Ce(III) derivatives, as molecular precursors for syntheses of nano-sized materials.

Custom Q&A

What is the molecular formula of glycine hydroxamate?

The molecular formula of glycine hydroxamate is C2H6N2O2.

What are some synonyms for glycine hydroxamate?

Some synonyms for glycine hydroxamate are 2-amino-N-hydroxyacetamide, acetamide, 2-amino-N-hydroxy-, and glycylhydroxamic acid.

What is the molecular weight of glycine hydroxamate?

The molecular weight of glycine hydroxamate is 90.08 g/mol.

What role does glycine hydroxamate have as an inhibitor?

Glycine hydroxamate has a role as an EC 1.4.4.2 [glycine dehydrogenase (aminomethyl-transferring)] inhibitor.

What is the IUPAC name of glycine hydroxamate?

The IUPAC name of glycine hydroxamate is 2-amino-N-hydroxyacetamide.

What is the InChIKey of glycine hydroxamate?

The InChIKey of glycine hydroxamate is VDBCTDQYMZSQFQ-UHFFFAOYSA-N.

What is the CAS number of glycine hydroxamate?

The CAS number of glycine hydroxamate is 5349-80-4.

How many hydrogen bond donor counts does glycine hydroxamate have?

Glycine hydroxamate has three hydrogen bond donor counts.

How many rotatable bond counts does glycine hydroxamate have?

Glycine hydroxamate has one rotatable bond count.

Is glycine hydroxamate a canonicalized compound?

Yes, glycine hydroxamate is a canonicalized compound.