136050-67-4

Basic information

• Product Name: FMOC-CYS(4-MBZL)-OH
• Synonyms: N-ALPHA-(9-FLUORENYLMETHYLOXYCARBONYL)-S-(4-METHYLBENZYL)-L-CYSTEINE;N-ALPHA-(9-FLUORENYLMETHOXYCARBONYL)-S-(4-METHYLBENZYL)-L-CYSTEINE;FMOC-S-4-METHYLBENZYL-L-CYSTEINE;FMOC-S-P-METHYLBENZYL-L-CYSTEINE;FMOC-CYS(4-CH3BZL)-OH;FMOC-CYS(4-MBZL)-OH;FMOC-CYS(4-MEBZL)-OH;FMOC-CYSTEINE(MBZL)-OH
• CAS NO: 136050-67-4
• Molecular Formula: C₂₆H₂₅NO₄S
• Molecular Weight: 447.55
• Product Categories: Amino Acids;Cysteine [Cys, C];Fmoc-Amino Acids and Derivatives
• Mol File: 136050-67-4.mol
• Article Data: 2

Chemical Properties

• Melting Point: 150-158 °C
• Boiling Point: 671.7oC at 760 mmHg
• Flash Point: 360oC
• Appearance: White Powder
• Density: 1.278g/cm3
• Vapor Pressure: 5.87E-19mmHg at 25°C
• Refractive Index: 1.638
• Storage Temp.: 2-8°C
• PKA: 3.46±0.10(Predicted)
• CAS DataBase Reference: FMOC-CYS(4-MBZL)-OH(CAS DataBase Reference)
• NIST Chemistry Reference: FMOC-CYS(4-MBZL)-OH(136050-67-4)
• EPA Substance Registry System: FMOC-CYS(4-MBZL)-OH(136050-67-4)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• F: 10
• Hazardous Substances Data: 136050-67-4(Hazardous Substances Data)

Usage

General Description

FMOC-CYS(4-MBZL)-OH is a chemical compound that consists of an FMOC (9-fluorenylmethoxycarbonyl) protecting group attached to a cysteine amino acid, which is further modified with a 4-mercaptobenzylamine (4-MBZL) group. FMOC-CYS(4-MBZL)-OH is commonly used in peptide synthesis and bioconjugation reactions. The FMOC group serves as a temporary protecting group for the cysteine thiol, allowing for specific chemical modifications to be made at the cysteine residue. The 4-MBZL modification offers a unique functional group for further conjugation or for studying the reactivity of cysteine residues in proteins. FMOC-CYS(4-MBZL)-OH is an important building block for the synthesis of peptide and protein conjugates for scientific research and therapeutic applications.

InChI:InChI=1/C26H25NO4S/c1-17-10-12-18(13-11-17)15-32-16-24(25(28)29)27-26(30)31-14-23-21-8-4-2-6-19(21)20-7-3-5-9-22(20)23/h2-13,23-24H,14-16H2,1H3,(H,27,30)(H,28,29)/t24-/m0/s1

Upstream product

• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 
• 135273-01-7 N,N'-bis[(9H-fluoren-9-ylmethoxy)carbonyl]-L-cystine 
• 135248-89-4 N^α-fluoren-9-ylmethoxycarbonyl-L-cysteine 
• 104-81-4 4-Methylbenzyl bromide 
• 42294-52-0 S-<(4-methylphenyl)methyl>-L-cysteine 

Downstream Products

• 152684-58-7 N^α-Fmoc-α-benzyl-γ-glutamyl--β-alanine ethyl ester 
• 1056710-12-3 3-[(R)-2-Amino-3-(4-methyl-benzylsulfanyl)-propionylamino]-propionic acid ethyl ester 

Relevant articles and documents

A comprehensive one-pot synthesis of protected cysteine and selenocysteine SPPS derivatives

A proof-of-principle methodology is presented in which all commercially-available cysteine (Cys) and selenocysteine (Sec) solid phase peptide synthesis (SPPS) derivatives are synthesized in high yield from easily prepared protected dichalcogenide precursors. A Zn-mediated biphasic reduction process applied to a series of four bis-Nα-protected dichalcogenide compounds allows facile conversion to their corresponding thiol and selenol intermediates followed by insitu S- or Se-alkylation with various electrophiles to directly access twenty one known Cys and Sec SPPS derivatives. Most of these derivatives were able to be precipitated in crude form out of petroleum ether in sufficient purity for direct use as peptide building blocks. Subsequent incorporation of these derivatives into peptide models nicely illustrates their viability and applicability toward SPPS.