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HomeProduct name listFMOC-S-trityl-L-cysteine

FMOC-S-trityl-L-cysteine

Synonym(s):N-(9-Fluorenylmethoxycarbonyl)-S-trityl-L-cysteine;Nα-Fmoc-S-trityl-L-cysteine;Fmoc-Cys(Trt)-OH;N-α-Fmoc-S-trityl-L-cysteine

  • CAS NO.:103213-32-7
  • Empirical Formula: C37H31NO4S
  • Molecular Weight: 585.71
  • MDL number: MFCD00038538
  • EINECS: 600-408-4
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-06-13 17:47:58
FMOC-S-trityl-L-cysteine Structural

What is FMOC-S-trityl-L-cysteine?

Chemical properties

white to light yellow crystal powde

The Uses of FMOC-S-trityl-L-cysteine

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.

The Uses of FMOC-S-trityl-L-cysteine

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. 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 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, as this has been shown to significantly reduce loss of optical integrity during coupling.

Properties of FMOC-S-trityl-L-cysteine

Melting point: 170-173 °C(lit.)
Boiling point: 763.4±60.0 °C(Predicted)
alpha  16 º (c=1, THF)
Density  1.270±0.06 g/cm3(Predicted)
refractive index  18 ° (C=1, THF)
storage temp.  2-8°C
solubility  Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
form  Powder
pka 3.70±0.10(Predicted)
color  White to almost white
optical activity [α]20/D +16.0±2°, c = 1% in THF
Water Solubility  Insoluble in water. Soluble in most organic solvents.
BRN  4221286
CAS DataBase Reference 103213-32-7(CAS DataBase Reference)

Safety information for FMOC-S-trityl-L-cysteine

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for FMOC-S-trityl-L-cysteine

InChIKey KLBPUVPNPAJWHZ-UMSFTDKQSA-N

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