8.52008

Fmoc-Cys(Trt)-OH

Novabiochem^®

• Synonym(s): Fmoc-Cys(Trt)-OH, N-α-Fmoc-S-trityl-L-cysteine
• Empirical Formula (Hill Notation): C₃₇H₃₁NO₄S
• CAS Number: 103213-32-7
• Molecular Weight: 585.71
• UNSPSC Code: 12352209
• NACRES: NA.22
• MDL number: MFCD00038538

Properties

• Quality Segment: 400
• 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.: 2-8°C
• 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

Description

General description

High purity Fmoc-protected amino acid for research and process production of peptides, with very low levels of dipeptide, free-amino acids and acetic acid impurities. 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.


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.

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).

Analysis Note

Colour (visual): white to off white
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.

Other Notes

Replaces: 04-12-1018

Legal Information

Novabiochem is a registered trademark of Merck KGaA, Darmstadt, Germany

PyBOP is a registered trademark of Merck KGaA, Darmstadt, Germany

Safety Information

• Storage Class: 11 - Combustible Solids
• flash_point_f: Not applicable
• flash_point_c: Not applicable