8.52008
Fmoc-Cys(Trt)-OH
Novabiochem®
Synonym(s):
Fmoc-Cys(Trt)-OH, N-α-Fmoc-S-trityl-L-cysteine
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About This Item
Product Name
Fmoc-Cys(Trt)-OH, Novabiochem®
SMILES string
S(C[C@H](NC(=O)OCC4c5c(cccc5)c6c4cccc6)C(=O)[O-])C(c3ccccc3)(c2ccccc2)c1ccccc1
InChI
1S/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)/p-1/t34-/m0/s1
InChI key
KLBPUVPNPAJWHZ-UMSFTDKQSA-M
product line
Novabiochem®
assay
≥98% (TLC)
≥98.0% (acidimetric)
≥99.0% (HPLC)
form
powder
reaction suitability
reaction type: Fmoc solid-phase peptide synthesis
manufacturer/tradename
Novabiochem®
mp
164-175 °C
application(s)
peptide synthesis
functional group
thiol
storage temp.
−20°C (−15°C to −25°C)
Quality Level
Analysis Note
Appearance of substance (visual): powder
Colour index (0,5 M in DMF): ≤ 150 Hazen
Identity (IR): passes test
Enantiomeric purity: ≥ 99.5 % (a/a)
Purity (HPLC): ≥ 99.0 % (a/a)
Fmoc-ß-Ala-OH (HPLC): ≤ 0.1 % (a/a)
Fmoc-ß-Ala-Cys (Trt) -OH (HPLC): ≤ 0.1 % (a/a)
Fmoc-Cys(Trt)-Cys(Trt)-OH (HPLC): ≤ 0.1 % (a/a)
Fmoc-Cys-OH (HPLC): ≤ 0.1 % (a/a)
Assay free amino acid (HPLC): ≤ 0.2 %
Purity (TLC(011A)): ≥ 98 %
Purity (TLC(0811)): ≥ 98 %
Solubility (1 mmole in 2 ml DMF): clearly soluble
Assay (acidimetric): ≥ 98.0 %
Water (K. F.): ≤ 2.0 %
Ethyl acetate (HS-GC): ≤ 0.5 %
Acetate (IC): ≤ 0.02 %
To see the solvent systems used for TLC of Novabiochem® products please click here.
Application
- On-resin synthesis of cyclic peptides via tandem N-to-S acyl migration and intramolecular thiol additive-free native chemical ligation: Discusses the use of Fmoc-Cys(Trt)-OH in the synthesis of cyclic peptides, highlighting the efficiency of the resin synthesis method. (Serra et al., 2020).
- Selective Bi‐directional Amide Bond Cleavage of N‐Methylcysteinyl Peptide: The study utilized Fmoc-Cys(Trt)-OH in exploring selective bi-directional amide bond cleavage in peptides, providing insights into controlled peptide modification. (Qiu et al., 2014).
General description
Associated Protocols and Technical Articles
Fmoc-amino acids for Peptide Production
Cleavage and Deprotection Protocols for Fmoc SPPS
Fmoc SPPS of Cysteine-Containing Peptides
Literature references
[1] S. N. McCurdy (1989) Pept. Res., 2, 147.
[2] T. Kaiser, et al. (1996) Tetrahedron Lett., 37, 1187.
[3] Y. X. Han, et al. (1997) J. Org. Chem., 62, 4307.
[4] Y. N. Angell (2002) J. Peptide Res., 5, 292.
Other Notes
Legal Information
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
Certificates of Analysis (COA)
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Protocols
Overcome challenges in synthesis and disulfide bond formation with protocols for Fmoc solid-phase peptide synthesis of peptides with cysteine and methionine.
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