N-Benzyloxycarbonylglycine

Base Information

• Chemical Name: N-Benzyloxycarbonylglycine
• CAS No.: 1138-80-3
• Deprecated CAS: 72100-98-2,409108-80-1
• Molecular Formula: C10H11NO4
• Molecular Weight: 209.202
• Hs Code.: 2924.29 DERIVATION
• European Community (EC) Number: 214-516-0
• NSC Number: 2526
• DSSTox Substance ID: DTXSID8061559
• Nikkaji Number: J80.195J
• Wikidata: Q27101958
• Metabolomics Workbench ID: 49857
• ChEMBL ID: CHEMBL101287
• Mol file: 1138-80-3.mol

Synonyms:Cbz-Gly;N-benzyloxycarbonylglycine;N-carbobenzoxyglycine;Z-Gly

Chemical Property of N-Benzyloxycarbonylglycine

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 6.05E-08mmHg at 25°C
• Melting Point: 118-122 °C(lit.)
• Refractive Index: 1.5400 (estimate)
• Boiling Point: 424 °C at 760 mmHg
• PKA: 3.98±0.10(Predicted)
• Flash Point: 210.2 °C
• PSA: 75.63000
• Density: 1.289 g/cm³
• LogP: 1.38830
• Storage Temp.: Store at RT.
• Solubility.: methanol: 0.1 g/mL, clear
• Water Solubility.: Soluble in methanol. Insoluble in water.
• XLogP3: 1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 209.06880783
• Heavy Atom Count: 15
• Complexity: 224

Purity/Quality:

99% ^*data from raw suppliers

N-Carbobenzoxyglycine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 62-36/37/38-20/21/22
• Safety Statements: 24/25-36-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Biological Agents -> Amino Acids and Derivatives
• Canonical SMILES: C1=CC=C(C=C1)COC(=O)NCC(=O)O
• General Description: N-Carbobenzyloxyglycine (also known as N-benzyloxycarbonylglycine or Z-Gly) is a glycine derivative where the amino group is protected by a benzyloxycarbonyl (Cbz) group. It serves as a key ligand in coordination chemistry, forming complexes with metal ions such as Zn(II), Cd(II), and Co(II). These complexes exhibit distinct geometries (e.g., tetrahedral, pentagonal-bipyramidal, or octahedral) and demonstrate enhanced antimicrobial activity compared to the free ligand, likely due to improved lipophilicity and membrane permeability. The Cd(II) complex, in particular, forms a polymeric structure and shows broad-spectrum activity against fungi and bacteria.

Technology Process of N-Benzyloxycarbonylglycine

There total 90 articles about N-Benzyloxycarbonylglycine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

tert-butyl N-(benzyloxycarbonyl)glycinate (16881-32-6) → N-(Benzyloxycarbonyl)glycine (1138-80-3)

Guidance literature:

With ytterbium(III) triflate; In nitromethane; at 45 - 50 ℃; for 5h;

Reference yield: 95.0%

benzyl 2-hydroxyethylcarbamate (77987-49-6) → N-(Benzyloxycarbonyl)glycine (1138-80-3)

Guidance literature:

With jones' reagent; In acetone; at 0 ℃; for 3h;

Reference yield: 94.0%

Z-Gly-NHNHPh (21855-71-0) → N-(Benzyloxycarbonyl)glycine (1138-80-3)

Guidance literature:

With oxygen; In acetonitrile; for 5h; tyrosinase, phosphate buffer pH 7;

DOI:10.1016/S0040-4039(99)00549-3

upstream raw materials:

benzyl chloroformate

glycine

acetic acid-[(25R)-5α-spirosta-7,9(11)-dien-3β-yl ester

Z-Gly-ONp

Downstream raw materials:

N-benzyloxycarbonyl-glycine p-nitrobenzyl ester

phenylmethyl 5-oxo-1,3-oxazolidine-3-carboxylate

N,N'-bis-benzyloxycarbonyl-N,N'-methanediyl-bis-glycine

[6-(4-nitro-phenyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-7-yl]-carbamic acid benzyl ester

Refernces

Syntheses, characterization and antimicrobial activity of the first complexes of Zn(II), Cd(II) and Co(II) with N-benzyloxycarbonylglycine. X-ray crystal structure of the polymeric Cd(II) complex

10.1016/j.ica.2007.06.041

The research investigates the synthesis, characterization, and antimicrobial properties of the first complexes formed between Zn(II), Cd(II), and Co(II) ions and N-benzyloxycarbonylglycine (N-Boc-glyH). The purpose of the study is to explore the coordination chemistry of these metal ions with N-Boc-glyH and to assess the potential antimicrobial activity of the resulting complexes. N-benzyloxycarbonylglycine (N-Boc-glyH) is the ligand used to form complexes with the metal ions. It serves as the coordinating molecule that binds to the metal centers in the Zn(II), Cd(II), and Co(II) complexes. Its presence is crucial for studying the coordination chemistry and antimicrobial properties of the resulting metal complexes. The metal salts were reacted with N-Boc-glyH in an ethanol-water mixture at pH 5–6 to form the complexes. The complexes were characterized using various techniques, including elemental analysis, IR spectroscopy, 1H and 13C NMR spectroscopy, and single-crystal X-ray diffraction for the Cd(II) complex. The study found that the complexes adopt different geometries: tetrahedral for Zn(II), distorted pentagonal-bipyramidal for Cd(II), and octahedral for Co(II). The Cd(II) complex forms a 2D supramolecular structure stabilized by non-covalent interactions. The antimicrobial assays revealed that the complexes, unlike the free ligand, inhibit the growth of Candida albicans, with the Cd(II) complex also showing activity against Aspergillus niger and certain bacteria. The study concludes that the coordination of N-Boc-glyH to metal ions enhances the antimicrobial activity, likely due to increased lipophilicity and permeation through microbial cell membranes.