3304-51-6

Basic information

• Product Name: N'-Cbz-L-ornithine
• Synonyms: L-ORNITHINE(CBZ);H-ORN(Z)-OH;H-ORN(CBZ)-OH;H-L-ORN(Z)-OH;N-D-CBZ-L-ORN;N-DELTA-Z-L-ORNITHINE;N-DELTA-BENZYLOXYCARBONYL-L-ORNITHINE;N-DELTA-CARBOBENZOXY-L-ORNITHINE
• CAS NO: 3304-51-6
• Molecular Formula: C₁₃H₁₈N₂O₄
• Molecular Weight: 266.29
• EINECS: 221-980-8
• Product Categories: Amino Acids;Ornithine [Org];Amino Acids and Derivatives;Z-Amino acid series
• Mol File: 3304-51-6.mol
• Article Data: 18

Chemical Properties

• Melting Point: 248-252℃
• Boiling Point: 492.2 °C at 760 mmHg
• Flash Point: 251.4 °C
• Appearance: /Solid
• Density: 1.234 g/cm³
• Vapor Pressure: 1.67E-10mmHg at 25°C
• Refractive Index: 1.556
• Storage Temp.: −20°C
• Solubility: Acidic Alcohol (Sparingly), Aqueous Acid (Slightly)
• PKA: 2.51±0.24(Predicted)
• CAS DataBase Reference: N'-Cbz-L-ornithine(CAS DataBase Reference)
• NIST Chemistry Reference: N'-Cbz-L-ornithine(3304-51-6)
• EPA Substance Registry System: N'-Cbz-L-ornithine(3304-51-6)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 3304-51-6(Hazardous Substances Data)

Usage

Description

N'-Cbz-L-ornithine, also known as Carbobenzyloxy-L-ornithine, is a chemical compound derived from L-ornithine, an amino acid. It is characterized by the presence of a carbobenzyloxy (Cbz) protecting group, which is commonly used in organic synthesis to protect the amino group of amino acids. This modification allows for selective reactions to occur at other sites on the molecule, making it a versatile building block in the synthesis of various biologically active compounds.

Uses

Used in Pharmaceutical Industry:
N'-Cbz-L-ornithine is used as a reactant in the synthesis of cyclic aminohexapeptides, which have demonstrated antifungal activity. This makes it a valuable component in the development of new antifungal drugs to combat fungal infections.
Used in Organic Synthesis:
Due to the presence of the Cbz protecting group, N'-Cbz-L-ornithine is used as a building block in the synthesis of various complex organic molecules, including pharmaceuticals, agrochemicals, and other bioactive compounds. The Cbz group allows for selective reactions to occur, facilitating the construction of intricate molecular structures.

InChI:InChI=1/C13H18N2O4/c14-11(12(16)17)7-4-8-15-13(18)19-9-10-5-2-1-3-6-10/h1-3,5-6,11H,4,7-9,14H2,(H,15,18)(H,16,17)/t11-/m0/s1

Upstream product

• 3184-13-2 L-ornithine hydrochloride 
• 501-53-1 benzyl chloroformate 
• 5874-56-6 For-DL-Orn(Z)-OH 
• 70-26-8 L-ornithine 
• 25693-00-9 (S)-2-Amino-5-{[1-phenyl-meth-(Z)-ylidene]-amino}-pentanoic acid 
• 16682-12-5 D-ornithine hydrochloride 

Downstream Products

• 115249-01-9 N²-(N-benzoyl-glycyl)-N⁵-benzyloxycarbonyl-L-ornithine 
• 83079-93-0 5-benzyloxycarbonylamino-2-oxo-valeric acid 
• 6205-08-9 N^α-acetyl-S-ornithine 
• 110414-90-9 N⁵-benzyloxycarbonyl-N²-(toluene-4-sulfonyl)-L-ornithine 
• 62631-17-8 Methyl N-δ-benzyloxycarbonyl-L-ornithinate 
• 53054-02-7 N_α-(1,1-dimethylethoxycarbonyl)-N_δ-(phenylmethoxycarbonyl)-L-ornithine 1,1-dimethylethyl ester 
• 53054-01-6 (S)-2-amino-5-(((benzyloxy)carbonyl)amino)pentanoic acid tert-butyl ester 
• 2480-93-5 Boc-Orn(Z)-OH 
• 25582-01-8 N^δ-Carbobenzoxy-N^α-caprylyl-Orn 
• 73995-50-3 H-Orn(Z)-OBzl 
• 76314-97-1 Nα-Hexadecanoyl-Nδ-benzyloxycarbonyl-L-ornithin 
• 5874-75-9 methyl (2S)-2-amino-5-[[(benzyloxy)carbonyl]amino]pentanoate hydrochloride 
• 121838-54-8 N^α,N^α-Dimethyl-N^δ-(benzyloxycarbonyl)ornithine 
• 138775-07-2 N^α-fluorenylmethyloxycarbonyl-N^δ-benzyloxycarbonylornithine 

Relevant articles and documents

A high optical activity chiral sea natural product synthesis method

The invention discloses a synthetic method for a chiral marine natural product with high optical activity. According to the method, a marine natural product with the high optical activity is prepared by adopting chiral amino acid. The method specifically comprises the following steps: first, using L-ornithine monohydrochloride and D-ornithine monohydrochloride as starting raw materials, and performing copper ion complexing, amino protecting, esterifying, urea forming and cyclizing to obtain an intermediate 5; then, using N-methylpyrrole as a raw material, and performing electrophilic reaction, hydrolyzing, acidizing and acylating in sequence to obtain an intermediate 9; finally, enabling the intermediate 5 and the intermediate 9 to react to prepare corresponding chiral natural products, namely (S)-midpacamide or (R)-midpacamide. According to the synthetic method, synthetic steps are simple; the operation is simple and convenient; reaction conditions are mild; the original structure of the product prepared by the provided synthetic route is kept; the optical purity of the obtained marine natural product is greater than 99 percent; the marine natural product has a wide application prospect.

Selection of amino acids and the biomimetic synthesis of amido bond in the presence of β-CD

A new method was developed to construct a special amido bond in the presence of β-cyclodextrin. This process is similar to peptide synthesis in organisms. NMR experiments were performed to investigate the possible mechanism. This work has potential application in biomimetic peptide synthesis.

Ca2+-induced folding of a chiral ditopic receptor based on a Pybox ligand and enhancement of anion recognition

A chiral Pybox ligand bearing two urea units was developed for a Ca 2+-induced folding ligand. 11 Ca2+ complexation of the Pybox ligand afforded chiral foldamer formation with coordination of the urea carbonyls to Ca2+. The halide-ion affinity of the foldamer was enhanced compared to Ca2+-free Pybox ligands.