103213-32-7

Basic information

• Product Name: FMOC-S-trityl-L-cysteine
• Synonyms: FMOC-CYSTEINE(TRT)-OH;FMOC-CYS(TRT);FMOC-CYS(TRT)-OH;FMOC-L-CYSTEINE(TRITYL);FMOC-L-CYSTEINE (TRT);FMOC-L-CYS(TRITYL);FMOC-L-CYS(TRT);FMOC-L-CYS(TRT)-OH
• CAS NO: 103213-32-7
• Molecular Formula: C₃₇H₃₁NO₄S
• Molecular Weight: 585.71
• EINECS: 600-408-4
• Product Categories: Pharmaceutical Intermediates;Fluorenes, Flurenones;Amino Acids;Cysteine [Cys, C];Fmoc-Amino Acids and Derivatives;Amino Acids (N-Protected);Biochemistry;Fmoc-Amino Acids;Fmoc-Amino acid series
• Mol File: 103213-32-7.mol
• Article Data: 5

Chemical Properties

• Melting Point: 170-173 °C(lit.)
• Boiling Point: 763.4 °C at 760 mmHg
• Flash Point: 415.5 °C
• Appearance: White to almost white/Powder
• Density: 1.27 g/cm³
• Vapor Pressure: 1.68E-24mmHg at 25°C
• Refractive Index: 18 ° (C=1, THF)
• Storage Temp.: 2-8°C
• PKA: 3.70±0.10(Predicted)
• Water Solubility: Insoluble in water. Soluble in most organic solvents.
• BRN: 4221286
• CAS DataBase Reference: FMOC-S-trityl-L-cysteine(CAS DataBase Reference)
• NIST Chemistry Reference: FMOC-S-trityl-L-cysteine(103213-32-7)
• EPA Substance Registry System: FMOC-S-trityl-L-cysteine(103213-32-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-26
• WGK Germany: 3
• F: 9-21
• Hazardous Substances Data: 103213-32-7(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powde

Uses

Different sources of media describe the Uses of 103213-32-7 differently. You can refer to the following data:
1. It is potentially useful for proteomics studies, and solid phase peptide synthesis techniques. Cysteine is versatile amino acid involved with many biological processes, including the formation of disulfide bonds - a critical component of protein structure. This compound could be useful as an unusual amino acid analog to aid in the deconvolution of protein structure and function.
2. Fmoc-Cys(Trt)-OH is an N-terminal protected cysteine derivative used in peptide synthesis. Some of the examples are:Synthesis of mono- and bi-functionalized platinum(IV) complexes to target angiogenic tumor vasculature.Synthesis of proteins through native chemical ligation of peptide hydrazides as thioester surrogates via solid-phase synthesis.Synthesis of glycoconjugates by conjugating reducing sugars to cysteine residues of peptides.

General Description

The standard derivative for Fmoc SPPS of peptides containing Cys [1]. The Trt group is removed with 95% TFA containing 1-5% TIS. Ideally, this derivative should be introduced using the symmetrical anhydride or DIPCDI/HOBt activation [2,3] to minimize enantiomerization. If activation with uronium or phosphonium reagents, such as HBTU or PyBOP?, is to be employed, it is strongly recommended that collidine is used as the base [4], as this has been shown to significantly reduce loss of optical integrity during coupling.The product number for this product was previously 04-12-1018.To obtain a certificate of analysis (CoA) of a lot that begins with the letter “A”, please select the option in the right hand menu “Request a COA for Lot#s starting with A”.

InChI:InChI=1/C37H31NO4S/c39-35(40)34(38-36(41)42-24-33-31-22-12-10-20-29(31)30-21-11-13-23-32(30)33)25-43-37(26-14-4-1-5-15-26,27-16-6-2-7-17-27)28-18-8-3-9-19-28/h1-23,33-34H,24-25H2,(H,38,41)(H,39,40)/t34-/m1/s1

Upstream product

• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 
• 76-83-5 trityl chloride 
• 2799-07-7 S-trityl-L-cysteine 
• 52-90-4 L-Cysteine 
• 135273-01-7 N,N'-bis[(9H-fluoren-9-ylmethoxy)carbonyl]-L-cystine 
• 135248-89-4 N^α-fluoren-9-ylmethoxycarbonyl-L-cysteine 

Downstream Products

• 501034-07-7 3,4-methylenedioxy-5,4'-dimethoxy-3'-(S-Trt-N^α-Fmoc-L-Cys)amido-Z-stilbene 
• 245088-56-6 Fmoc-Cys(Trt)-OMe 
• 370857-83-3 Fmoc-Cys(Trt)-N(CH₃)-OCH₃ 
• 639066-17-4 C₄₉H₅₅NO₄S 

Relevant articles and documents

Investigation of Cysteine as an Activator of Side-Chain N→S Acyl Transfer and Tail-to-Side-Chain Cyclization

N→S Acyl transfer is a popular method for the postsynthesis production of peptide C α -thioesters for use in native chemical ligation and for the synthesis of head-to-tail cyclic peptides. Meanwhile thioester formation at the side chain of aspartic or glutamic acids, leading to tail-to-side-chain-cyclized species, is less common. Herein we explore the potential for cysteine to function as a latent thioester when appended to the side chain of glutamic acid. Initial insights gained through study of C-terminal β-alanine as a model for the increased chain length were ultimately applied to peptide macrocyclization. Our results emphasize the increased barrier to acyl transfer at the glutamic acid side chain and indicate how a slow reaction, facilitated by cysteine itself, may be accelerated by fine-tuning of the stereoelectronic environment..

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.

Treating disorders by application of insulin-like growth factors and analogs

A method of enhancing the survival of neuronal cells in a mammal, the cells being at risk of dying, the method including the step of administering to the mammal one of the following substances: IGF-I; a functional derivative of IGF-I; IGF-II; a functional derivative of IGF-II; IGF-III; or a functional derivative of IGF-III.