53298-33-2

Basic information

• Product Name: FMOC-CYS(BZL)-OH
• Synonyms: FMOC-(S)-BENZYL-L-CYS;FMOC-S-BENZYL-L-CYSTEINE;FMOC-(S)-2-AMINO-3-(S-BENZYLTHIO)PROPANOIC ACID;FMOC-CYS(BZL)-OH;FMOC-CYSTEINE(BZL)-OH;N-ALPHA-FMOC-S-BENZYL-L-CYSTEINE;L-Cysteine-3-13C-N-FMOC, S-Benzyl;N-alpha-(9-Fluorenylmethyloxycarbonyl)-S-benzyl-L-cysteine
• CAS NO: 53298-33-2
• Molecular Formula: C₂₅H₂₃NO₄S
• Molecular Weight: 433.52
• Mol File: 53298-33-2.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 663.173 °C at 760 mmHg
• Flash Point: 354.874 °C
• Appearance: /Solid
• Density: 1.298 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.645
• Storage Temp.: Store at RT.
• PKA: 3.47±0.10(Predicted)
• CAS DataBase Reference: FMOC-CYS(BZL)-OH(CAS DataBase Reference)
• NIST Chemistry Reference: FMOC-CYS(BZL)-OH(53298-33-2)
• EPA Substance Registry System: FMOC-CYS(BZL)-OH(53298-33-2)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 53298-33-2(Hazardous Substances Data)

Usage

General Description

FMOC-CYS(BZL)-OH is a chemical compound that consists of a fluorenylmethyloxycarbonyl (FMOC) protecting group, a cysteine amino acid with a benzyl (BZL) protecting group, and a carboxylic acid functional group. The FMOC group is commonly used in peptide synthesis to protect the amine group of amino acids, while the BZL group is used to protect the thiol group of cysteine. FMOC-CYS(BZL)-OH is often used in the solid-phase synthesis of peptides, where the FMOC group can be selectively removed to expose the amine group for coupling to the next amino acid. Additionally, the presence of the BZL group allows for selective deprotection of the thiol group under mild conditions without affecting other functional groups, making it a valuable tool in peptide chemistry.

InChI:InChI=1/C25H23NO4S/c27-24(28)23(16-31-15-17-8-2-1-3-9-17)26-25(29)30-14-22-20-12-6-4-10-18(20)19-11-5-7-13-21(19)22/h1-13,22-23H,14-16H2,(H,26,29)(H,27,28)/t23-/m0/s1

Upstream product

• 3054-01-1 S-benzyl-L-cysteine 
• 88744-04-1 (9-fluorenyl)methyl pentafluorophenyl carbonate 
• 28920-43-6 (fluorenylmethoxy)carbonyl chloride 
• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 
• 135273-01-7 N,N'-bis[(9H-fluoren-9-ylmethoxy)carbonyl]-L-cystine 
• 100-39-0 benzyl bromide 
• 135248-89-4 N^α-fluoren-9-ylmethoxycarbonyl-L-cysteine 

Downstream Products

• 82176-99-6 N-(((9H-fluoren-9-yl)methoxy)carbonyl)-S-((3-nitropyridin-2-yl)thio)-L-cysteine 
• 256957-78-5 H-Gly-L-Cys-Phe-NH₂ 
• 1429056-90-5 C₃₅H₃₈N₂O₉S 
• 140684-98-6 Fmoc-Ser(Bzl)-Cys(Bzl)-O^tBu 
• 140684-99-7 H-Ser(Bzl)-Cys(Bzl)-O^tBu 
• 70375-25-6 (R) tert-butyl-2-amino-3-(benzylthio)propionate 
• 147220-17-5 (S)-4-[(R)-2-Benzylsulfanyl-1-(2-ethoxycarbonyl-ethylcarbamoyl)-ethylcarbamoyl]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid benzyl ester 
• 152684-53-2 (S)-γ-glutamyl-(R)-S-(benzyl)cysteinyl-(R)-phenylglycine 
• 803653-08-9 3-((R)-2-Amino-3-benzylsulfanyl-propionylamino)-propionic acid ethyl ester 
• 140702-14-3 Fmoc-Cys(Bzl)-O^tBu 
• 103321-55-7 Fmoc-Cys(Bzl)-Cl 
• 147220-16-4 3-[(R)-3-Benzylsulfanyl-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionylamino]-propionic acid ethyl ester 

Relevant articles and documents

Amino Acids Bearing Aromatic or Heteroaromatic Substituents as a New Class of Ligands for the Lysosomal Sialic Acid Transporter Sialin

Sialin, encoded by the SLC17A5 gene, is a lysosomal sialic acid transporter defective in Salla disease, a rare inherited leukodystrophy. It also enables metabolic incorporation of exogenous sialic acids, leading to autoantibodies against N-glycolylneuraminic acid in humans. Here, we identified a novel class of human sialin ligands by virtual screening and structure-activity relationship studies. The ligand scaffold is characterized by an amino acid backbone with a free carboxylate, an N-linked aromatic or heteroaromatic substituent, and a hydrophobic side chain. The most potent compound, 45 (LSP12-3129), inhibited N-acetylneuraminic acid 1 (Neu5Ac) transport in a non-competitive manner with IC50 ≈ 2.5 μM, a value 400-fold lower than the KM for Neu5Ac. In vitro and molecular docking studies attributed the non-competitive character to selective inhibitor binding to the Neu5Ac site in a cytosol-facing conformation. Moreover, compound 45 rescued the trafficking defect of the pathogenic mutant (R39C) causing Salla disease. This new class of cell-permeant inhibitors provides tools to investigate the physiological roles of sialin and help develop pharmacological chaperones for Salla disease.

9-Fluorenylmethyl Pentafluorophenyl Carbonate as a Useful Reagent for the Preparation of N-9-Fluorenylmethyloxycarbonylamino Acids and their Pentafluorophenyl Esters

9-Fluorenylmethyl pentafluorophenyl carbonate is a useful reagent for the efficient, side reaction-free introduction of N-9-fluorenylmethyloxycarbonyl protecting group into amino acids and for the subsequent preparation of their pentafluorophenyl esters.Some new compounds of both types are described.