133174-15-9

Basic information

• Product Name: Fmoc-L-citrulline
• Synonyms: Nα-[(9H-Fluoren-9-ylMethoxy)carbonyl]-L-citrulline;(S)-2-((((9H-fluoren-9-yl)Methoxy)carbonyl)aMino)-5-ureidopentanoic acid;Fmoc-Cit-OH >=97.0% (HPLC);(S)-2-Fmoc-amino-5-ureidopentanoic acid;Fmoc-L-citrulline≥ 98% (HPLC);Fmoc-L-Orn(carbamoyl)-OH;FMOC-ORN(CARBAMOYL)-OH;FMOC-L-2-AMINO-5-UREIDO-N-VALERIC ACID
• CAS NO: 133174-15-9
• Molecular Formula: C21H23N3O5
• Molecular Weight: 397.42
• Product Categories: Amino Acids;Citruline [Cit];Unusual Amino Acids;Fmoc-Amino acid series
• Mol File: 133174-15-9.mol

Chemical Properties

• Boiling Point: 671.5oC at 760 mmHg
• Flash Point: 359.9oC
• Appearance: /Solid
• Density: 1.316g/cm3
• Vapor Pressure: 6.01E-19mmHg at 25°C
• Refractive Index: -10 ° (C=1, DMF)
• Storage Temp.: 2-8°C
• PKA: 3.84±0.21(Predicted)
• BRN: 7780987
• CAS DataBase Reference: Fmoc-L-citrulline(CAS DataBase Reference)
• NIST Chemistry Reference: Fmoc-L-citrulline(133174-15-9)
• EPA Substance Registry System: Fmoc-L-citrulline(133174-15-9)

Safety Data

• WGK Germany: 3
• F: 10
• HazardClass: IRRITANT
• Hazardous Substances Data: 133174-15-9(Hazardous Substances Data)

Usage

Chemical Properties

White powder

InChI:InChI=1/C21H23N3O5/c22-20(27)23-11-5-10-18(19(25)26)24-21(28)29-12-17-15-8-3-1-6-13(15)14-7-2-4-9-16(14)17/h1-4,6-9,17-18H,5,10-12H2,(H,24,28)(H,25,26)(H3,22,23,27)/t18-/m0/s1

Upstream product

• 372-75-8 Citrulline 
• 28920-43-6 (fluorenylmethoxy)carbonyl chloride 

Downstream Products

• 776305-25-0 2-(2-{3-[1-(4-bromo-phenyl)-ethyl]-ureido}-5-ureido-pentanoylamino)-3-methyl-butyric acid 

Relevant articles and documents

A Wireframe DNA Cube: Antibody Conjugate for Targeted Delivery of Multiple Copies of Monomethyl Auristatin E

In recent years, several antibody drug conjugates (ADC) have been accepted by the FDA as therapeutics against cancer. It is well-known that control of drug-to-antibody ratio (DAR) is vital for the success of an ADC, which inspires the advancement of bette

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.

DRUG-LINKER CONJUGATE PHARMACEUTICAL COMPOSITIONS

Compositions are disclosed having a cytotoxic and/or vascular disrupting agent (VDA) payload attached to a linker. The linker can be a cathepsin B protease cleavable linker or a non-cleavable linker that may degrade intracellularly. Methods for making and using the compositions are also provided. The compositions can be provided to a patient in need thereof with the composition coming into contact with a cancer cell to activate or release the cytotoxic and/or vascular disrupting agent payload.

SILVESTROL ANTIBODY-DRUG CONJUGATES AND METHODS OF USE

The invention relates generally to a silvestrol molecule activated with a leaving group. The invention further relates generally to an antibody-drug conjugate comprising an antibody conjugated by a linker to one or more silvestrol drug moieties and methods of treatment.

QUATERNARY AMINE COMPOUNDS AND ANTIBODY-DRUG CONJUGATES THEREOF

This invention relates to antibody-drug conjugates represented by Formula (I) Ab- (L-D)p, Ab is an antibody; p is 1-8; L-D is a chemical moiety represented by the following formula -Str-(Pep)-Sp-D; Str is a stretcher unit covalently attached to Ab; Pep is a linker; D is anti-tumor agent represented by the following formula wherein Rand Rare each independently Ct-C6alkyl, and Ris a non-hydrogen substituent; or Ris C1-C6alkyl, and Rand Rtogether with the N form a substituted C3-C7heterocycloalkyl ring; or R° is absent, and Rand Rtogether with the N form a substituted heteroaryl ring; Sp-D is a spacer moiety of fomula: This invention also relates to a method of treating cancer, use of antibody-drug conjugates of Formula (I) in therapy, and use of antibody-drug conjugates of Formula (I) in manufacturing a medicament for treating cancer. This invention also relates to method of preparing antibody-drug conjugates of Formula (I).

ANTI-STAPHYLOCOCCUS AUREUS ANTIBODY RIFAMYCIN CONJUGATES AND USES THEREOF

The invention provides anti-Staphylococcus aureus antibody rifamycin antibiotic conjugates and methods of using same.

ANTI-STAPHYLOCOCCUS AUREUS ANTIBODY RIFAMYCIN CONJUGATES AND USES THEREOF

The invention provides rF1 antibody antibiotic conjugates and methods of using same.

ANTIBODIES AND IMMUNOCONJUGATES

The invention provides immunoconjugates and methods of using the same.

LINKERS AND APPLICATION TOWARDS ADC THEREOF

Disclosed are linkers, containing amide surrogates with a regular or novel lysosomal enzymatic cleavable dipeptidic unit, to connect cytotoxic drugs to antibodies. Also disclosed are ADCs (antibody-drug conjugates) derived from these amide surrogate linke

PEPTIDOMIMETIC COMPOUNDS AND ANTIBODY-DRUG CONJUGATES THEREOF

This invention relates to peptidomimetic linkers and anti-body drug conjugates thereof, to pharmaceutical compositions containing them, and to their use in therapy for the prevention or treatment of cancer.