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
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) |
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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