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
• Article Data: 7

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

Chemical Properties

Light yellow powder

Uses

Fmoc-cys(acm)-oh, is an amino acid building block used in peptide synthesis. With a growing peptide drug market the fast, reliable synthesis of peptides is of great importance.

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

• 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 
• 718635-75-7 Fmoc-Cys(Acm)-OMe 
• 19647-70-2 S-acetamidomethyl-L-cysteine 
• 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 
• 28920-43-6 (fluorenylmethoxy)carbonyl chloride 

Downstream Products

• 1014987-55-3 C₅₈H₈₀N₁₄O₁₅S₂ 
• 1610953-24-6 C₆₆H₁₀₇N₁₇O₂₄S₃ 
• 1610953-19-9 C₆₆H₁₀₇N₁₇O₂₄S₃ 
• 1610953-22-4 C₆₆H₁₀₇N₁₇O₂₄S₃ 
• 1314096-88-2 Fmoc-[Cys(N-acetamidomethyl),(2,7)Cys(N-methyl-phenacyloxycarbamidomethyl)(3)]-α-conotoxin SI(1-8)-(4-SC6H4CH2COOH) 

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.

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.

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.