45234-13-7

Basic information

• Product Name: BOC-CIT-OH
• Synonyms: NALPHA-BOC-L-CITRULLINE;N-ALPHA-T-BUTOXYCARBONYL-L-CITRULLINE;N-ALPHA-T-BUTOXYCARBONYL, DELTA-CARBAMOYL-L-ORNITHINE;nα-boc-l-citrulline;Boc-L-Cit-OH;NALPHA-tert-Butoxycarbonyl-L-citrulline;N-Boc-Cit-OH;(S)-2-((tert-Butoxycarbonyl)aMino)-5-ureidopentanoic acid
• CAS NO: 45234-13-7
• Molecular Formula: C₁₁H₂₁N₃O₅
• Molecular Weight: 275.3
• Mol File: 45234-13-7.mol
• Article Data: 5

Chemical Properties

• Melting Point: ~60 °C
• Boiling Point: 483 °C at 760 mmHg
• Flash Point: 245.9 °C
• Appearance: /
• Density: 1.212 g/cm³
• Vapor Pressure: 1.17E-10mmHg at 25°C
• Refractive Index: 1.502
• Storage Temp.: 2-8°C
• Solubility: DMSO
• PKA: 3.95±0.21(Predicted)
• CAS DataBase Reference: BOC-CIT-OH(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-CIT-OH(45234-13-7)
• EPA Substance Registry System: BOC-CIT-OH(45234-13-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• F: 3-10
• HazardClass: IRRITANT
• Hazardous Substances Data: 45234-13-7(Hazardous Substances Data)

Usage

Chemical Properties

White to pale yellow powder

Uses

Boc-L-citrulline is an intermediate in the synthesis of Arginino-succinic Acid Disodium Salt (A769200). Arginino-succinic Acid Sodium Salt is used in the characterization of δ-crystallin in avian species.

InChI:InChI=1/C11H21N3O5/c1-11(2,3)19-10(18)14-7(8(15)16)5-4-6-13-9(12)17/h7H,4-6H2,1-3H3,(H,14,18)(H,15,16)(H3,12,13,17)/t7-/m0/s1

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 372-75-8 Citrulline 

Downstream Products

• 1037793-80-8 (S)-tert-butyl 1-(4-(hydroxymethyl)phenylamino)-1-oxo-5-ureidopentan-2-ylcarbamate 
• 1032291-87-4 l-citrulline-d-amphetamine hydrochloride 
• 1032291-88-5 Boc-Cit-Amp 
• 149970-88-7 tert-butyl N^α-Boc-N^G-(benzyloxy)-L-arginate 
• 133565-48-7 N^ω-Hydroxy-L-arginine dihydrochloride 

Relevant articles and documents

Bivalent EGFR-Targeting DARPin-MMAE Conjugates

Epidermal growth factor receptor (EGFR) is a validated tumor marker overexpressed in various cancers such as squamous cell carcinoma (SSC) of the head and neck and gliomas. We constructed protein-drug conjugates based on the anti-EGFR Designed Ankyrin Repeat Protein (DARPin) E01, and compared the bivalent DARPin dimer (DD1) and a DARPin-Fc (DFc) to the monomeric DARPin (DM) and the antibody derived scFv425-Fc (scFvFc) in cell culture and a mouse model. The modular conjugation system, which was successfully applied for the preparation of protein-drug and-dye con-jugates, uses bio-orthogonal protein-aldehyde generation by the formylglycine-generating enzyme (FGE). The generated carbonyl moiety is addressed by a bifunctional linker with a pyrazolone for a tandem Knoevenagel reaction and an azide for strain-promoted azide-alkyne cycloaddition (SPAAC). The latter reaction with a PEGylated linker containing a dibenzocyclooctyne (DBCO) for SPAAC and monomethyl auristatin E (MMAE) as the toxin provided the stable conjugates DD1-MMAE (drug-antibody ratio, DAR = 2.0) and DFc-MMAE (DAR = 4.0) with sub-nanomolar cytotoxicity against the human squamous carcinoma derived A431 cells. In vivo imaging of Alexa Fluor 647-dye conjugates in A431-xenografted mice bearing subcutaneous tumors as the SCC model revealed unspe-cific binding of bivalent DARPins to the ubiquitously expressed EGFR. Tumor-targeting was verified 6 h post-injection solely for DD1 and scFvFc. The total of four administrations of 6.5 mg/kg DD1-MMAE or DFc-MMAE twice weekly did not cause any sequela in mice. MMAE conjugates showed no significant anti-tumor efficacy in vivo, but a trend towards increased necrotic areas (p = 0.2213) was observed for the DD1-MMAE (n = 5).

Branched Linker for Protein Drug Conjugates

The present invention relates to method for connecting a protein and a drug to a protein drug conjugate, wherein the drug is linked to the protein through a specific branched linker, said branched linker comprises a peptide chain and is derived from o-hydroxy p-amino benzylic alcohol, wherein the peptide chain is connected to the phenyl ring via the p-amino group, the drug is connected to the phenyl ring via the benzylic alcohol moiety, and the protein is connected to the phenyl ring via the o-hydroxy group; further to a process for the preparation of said protein-drug-conjugates via various intermediates, to the pharmaceutical use of such protein drug conjugates, such as methods of controlling the growth of undesirable cells, to pharmaceutical compositions comprising such protein drug conjugates, and to intermediates of the preparation of the protein drug conjugates.

Methodology for the Preparation of N-Guanidino-Modified Arginines and Related Derivatives

Methods for the preparation of NG-modified arginines and Nδ-heterocyclic ornithines are described.The reactive cyanamide intermediate tert-butyl Nα-Boc-Nδ-cyano-L-ornithinate (2), prepared either by treatment of