6692-89-3

Basic information

• Product Name: N5-(aminocarbonyl)-N2-[(phenylmethoxy)carbonyl]-L-ornithine
• Synonyms: N5-(aminocarbonyl)-N2-[(phenylmethoxy)carbonyl]-L-ornithine;N5-Carbamoyl-N2-[(benzyloxy)carbonyl]-L-ornithine;(S)-2-(((Benzyloxy)carbonyl)amino)-5-ureidopentanoic acid;Na-Benzyloxycarbonyl-L-citrulline
• CAS NO: 6692-89-3
• Molecular Formula: C₁₄H₁₉N₃O₅
• Molecular Weight: 309.31776
• EINECS: 229-736-2
• Mol File: 6692-89-3.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 569.6°C at 760 mmHg
• Flash Point: 298.3°C
• Appearance: /
• Density: 1.298g/cm³
• Vapor Pressure: 8.17E-14mmHg at 25°C
• Refractive Index: 1.565
• Storage Temp.: 2-8°C
• CAS DataBase Reference: N5-(aminocarbonyl)-N2-[(phenylmethoxy)carbonyl]-L-ornithine(CAS DataBase Reference)
• NIST Chemistry Reference: N5-(aminocarbonyl)-N2-[(phenylmethoxy)carbonyl]-L-ornithine(6692-89-3)
• EPA Substance Registry System: N5-(aminocarbonyl)-N2-[(phenylmethoxy)carbonyl]-L-ornithine(6692-89-3)

Safety Data

• Hazardous Substances Data: 6692-89-3(Hazardous Substances Data)

Usage

General Description

N5-(aminocarbonyl)-N2-[(phenylmethoxy)carbonyl]-L-ornithine is a chemical compound that belongs to the class of ornithine derivatives. It is a derivative of the amino acid ornithine, which plays a key role in the urea cycle and the biosynthesis of proteins. This specific compound contains a carbonyl group and an amino group, as well as a phenylmethoxy group attached to the N2 position of the ornithine molecule. It may have potential applications in biochemical research or pharmaceutical development, and its properties and biological effects could be of interest for further investigation.

InChI:InChI=1/C14H19N3O5/c15-13(20)16-8-4-7-11(12(18)19)17-14(21)22-9-10-5-2-1-3-6-10/h1-3,5-6,11H,4,7-9H2,(H,17,21)(H,18,19)(H3,15,16,20)/t11-/m0/s1

Upstream product

• 3184-13-2 L-ornithine hydrochloride 
• 372-75-8 2-Amino-5-ureido-pentanoic acid 
• 501-53-1 benzyl chloroformate 
• 13139-17-8 N-(Benzyloxycarbonyloxy)succinimide 
• 372-75-8 Citrulline 

Downstream Products

• 89499-13-8 methyl N^α-benzyloxycarbonyl-L-citrullinate 
• 159857-79-1 (2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide 
• 159857-80-4 6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)-N-((S)-1-(((S)-1-((4-(hydroxymethyl)phenyl)amino)-1-oxo-5-ureidopentan-2-yl)amino)-3-methyl-1-oxobutan-2-yl)hexanamide 
• 125735-06-0 α-(benzyloxycarbonyl)arginino>succinic acid trimethyl ester 
• 125735-11-7 2-Benzyloxycarbonylamino-5-(2-imino-4-methoxycarbonylmethyl-5-oxo-imidazolidin-1-yl)-pentanoic acid methyl ester 
• 125735-10-6 2-Benzyloxycarbonylamino-5-(5-methoxycarbonylmethyl-4-oxo-4,5-dihydro-1H-imidazol-2-ylamino)-pentanoic acid methyl ester 
• 125735-05-9 N^α-(benzyloxycarbonyl)-N^δ-cyanoornithine methyl ester 
• 83575-47-7 benzyloxycarbonyl-D-phenylalanyl-L-prolyl-L-citrulline p-nitroanilide 
• 83575-45-5 L-prolyl-L-citrulline p-nitroanilide hydrobromide 
• 83575-46-6 benzyloxycarbonylglycyl-L-prolyl-L-citrulline p-nitroanilide 
• 83575-44-4 benzyloxycarbonyl-L-prolyl-L-citrulline p-nitroanilide 
• 89499-14-9 methyl N^α-benzyloxycarbonyl-N^ω-carbamoyl-L-citrullinate 
• 38150-56-0 3-(benzyloxycarbonylamido)-piperidin-2-one 
• 83575-38-6 N₁-carbamoyl-3-benzyloxycarbonylamidopiperidin-2-one 

Relevant articles and documents

Improved Methodology for the Synthesis of a Cathepsin B Cleavable Dipeptide Linker, Widely Used in Antibody-Drug Conjugate Research

Antibody-drug conjugates (ADCs) represent an emerging class of biopharmaceutical agents that deliver highly potent anticancer agents (payloads) selectively to tumors or components associated with the tumor microenvironment. The linker, responsible for the connection between the antibody and payload, is a crucial component of ADCs. In certain examples the linker is composed of a cleavable short peptide which imparts an additional aspect of selectivity. Especially prevalent is the cathepsin B cleavable Mc-Val-Cit-PABOH linker utilized in many pre-clinical ADC candidates, as well as the FDA approved ADC ADCETRIS (brentuximab vedotin). An alternative route for the synthesis of the cathepsin B cleavable Mc-Val-Cit-PABOH linker is reported herein that involved six steps from l-Citrulline and proceeded with a 50% overall yield. In this modified route, the spacer (a para-aminobenzyl alcohol moiety) was incorporated via HATU coupling followed by dipeptide formation. Importantly, this route avoided undesirable epimerization and proceeded with improved overall yield. Utilizing this methodology, a drug-linker construct incorporating a potent small-molecule inhibitor of tubulin polymerization (referred to as KGP05), was synthesized as a representative example.