86060-81-3

Basic information

• Product Name: Fmoc-S-acetamidomethyl-L-cysteine
• Synonyms: FMOC-L-CYSTEINE(ACM);FMOC-L-CYS(ACM)-OH;FMOC-L-CYS(ACM);FMOC-CYSTEINE(ACM)-OH;FMOC-CYS(ACM);FMOC-CYS(ACM)-OH;FMOC-S-ACETAMIDOMETHYL-L-CYSTEINE;9-FLUORENYLMETHOXYCARBONYL-S-ACETAMIDOMETHYL-L-CYSTEINE
• CAS NO: 86060-81-3
• Molecular Formula: C21H22N2O5S
• Molecular Weight: 414.47
• Product Categories: Amino Acid Derivatives;Amino Acids;Cysteine [Cys, C];Fmoc-Amino Acids and Derivatives;Fmoc-Amino acid series
• Mol File: 86060-81-3.mol

Chemical Properties

• Melting Point: 147-150 °C
• Boiling Point: 714.1 °C at 760 mmHg
• Flash Point: 385.7 °C
• Appearance: white or off-white crystalline powder
• Density: 1.327 g/cm³
• Vapor Pressure: 2.11E-21mmHg at 25°C
• Refractive Index: 1.618
• Storage Temp.: 2-8°C
• PKA: 3.43±0.10(Predicted)
• BRN: 4725388
• CAS DataBase Reference: Fmoc-S-acetamidomethyl-L-cysteine(CAS DataBase Reference)
• NIST Chemistry Reference: Fmoc-S-acetamidomethyl-L-cysteine(86060-81-3)
• EPA Substance Registry System: Fmoc-S-acetamidomethyl-L-cysteine(86060-81-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 86060-81-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Fmoc-S-acetamidomethyl-L-cysteine is used as a key building block for the synthesis of therapeutic peptides and proteins. Its unique structure allows for the incorporation of L-cysteine residues into peptide sequences with improved stability and solubility, which is essential for the development of effective peptide-based drugs.
Used in Research and Development:
In the field of research and development, Fmoc-S-acetamidomethyl-L-cysteine serves as an important tool for the synthesis of novel peptide sequences with potential biological activities. Its use in the development of new therapeutic agents and the study of peptide-protein interactions contributes to the advancement of biomedical sciences.
Used in Peptide Drug Market:
With the growing peptide drug market, the fast and reliable synthesis of peptides is of great importance. Fmoc-S-acetamidomethyl-L-cysteine plays a vital role in this process, as it enables the efficient and accurate assembly of peptide sequences, leading to the production of high-quality peptide-based drugs.
Used in Peptide Synthesis Education:
Fmoc-S-acetamidomethyl-L-cysteine is also utilized in educational settings, where it serves as a valuable teaching tool for students learning about peptide synthesis and the role of amino acid building blocks in the development of pharmaceuticals and other biotechnological applications.

InChI:InChI=1/C21H22N2O5S/c1-13(24)22-12-29-11-19(20(25)26)23-21(27)28-10-18-16-8-4-2-6-14(16)15-7-3-5-9-17(15)18/h2-9,18-19H,10-12H2,1H3,(H,22,24)(H,23,27)(H,25,26)/t19-/m1/s1

Upstream product

• 19647-70-2 S-acetamidomethyl-L-cysteine 
• 28920-43-6 (fluorenylmethoxy)carbonyl chloride 
• 28920-44-7 (9H-fluoren-9-yl)methyl azidoformate 
• 111082-99-6 (R)-3-(Acetylamino-methylsulfanyl)-2-amino-propionic acid; compound with trifluoro-methanesulfonic acid 
• 718635-75-7 Fmoc-Cys(Acm)-OMe 
• 135248-89-4 N^α-fluoren-9-ylmethoxycarbonyl-L-cysteine 
• 625-51-4 N-(hydroxymethyl)acetamide 
• 135273-01-7 N,N'-bis[(9H-fluoren-9-ylmethoxy)carbonyl]-L-cystine 
• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 

Downstream Products

• 113534-22-8 Fmoc-Cys(Acm)-OTDO 
• 86060-96-0 FmocCys(Acm)OPfp 
• 104523-33-3 1,6>-oxytocin 
• 145362-69-2 C₄₃H₆₂N₁₀O₁₆S₂ 

Relevant articles and documents

MgI2-chemoselective cleavage for removal of amino acid protecting groups: A fresh vision for peptide synthesis

In the field of peptide synthesis, the key to a successful access to synthetic targets lies on a pertinent combination of protecting groups. Their choice is directed by their selective removal conditions. We present here the behavior of some of the most used protecting groups in peptide chemistry under experimental cleavage conditions, combining MgI2 with MW irradiation, using 2-Me-THF as a green solvent. In these experimental conditions, the benzyloxycarbonyl protecting group as well as the Merrifield resin can be re-considered in peptide chemistry.

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.

Treatment of obesity

A method for the treatment of obesity in an animal such as a human, comprises administering to the animal an effective amount of a peptide which comprises an analogue of the carboxyl-terminal sequence of a growth hormone, particularly an analogue of the carboxyl-terminal sequence of human growth hormone containing amino acid residues 177-191. A pharmaceutical composition for use in the treatment of obesity is also disclosed.

Alternative and chemoselective deprotection of the α-amino and carboxy functions of N-Fmoc-amino acid and N-Fmoc-dipeptide methyl esters by modulation of the molar ratio in the AlCl3/N,N-dimethylaniline reagent system

The amino and carboxy functions in N-Fmoc-α-amino acid and N-Fmoc-peptide methyl esters can be alternatively and chemoselectively deprotected by treatment with the reagent system AlCl3/N,N- dimethylaniline (DMA). The chemoselectivity of the process is controlled by modulating the relative molar ratio of the Lewis acid and DMA. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

One-Pot Synthesis of S-Acetamidomethyl-N-fluorenylmethoxycarbonyl-L-cysteine (Fmoc-Cys(Acm)-OH)

A new strategy for the preparation of S-acetamidomethyl-N-fluorenylmethoxycarbonyl-L-cysteine is reported.Inexpensive, readily available reagents are used, and no special equipment is required.A very homogenous product is obtained after a simple crystallization at the end of the process, without purification of intermediates.

Peptide Synthesis. Part 6. Protection of the Sulphydryl Group of Cysteine in Solid-phase Synthesis using Nα-Fluorenylmethoxycarbonylamino Acids. Linear Oxytocin Derivatives

The Nα-fluorenylmethoxycarbonyl derivatives of S-acetamidomethyl-, S-t-butyl-, and S-S-t-butyl-cysteine have been prepared and used in solid-phase peptide synthesis on polar, poly(dimethylacrylamide) supports.All three derivatives proved suitable as judged by synthesis of the linear oxytocin nonapeptide amide sequence.