8.52007

Fmoc-Cys(tBu)-OH

Novabiochem^®

• Synonym(s): Fmoc-Cys(tBu)-OH, N-α-Fmoc-S-t.-butyl-L-cysteine
• Empirical Formula (Hill Notation): C₂₂H₂₅NO₄S
• CAS Number: 67436-13-9
• Molecular Weight: 399.50
• UNSPSC Code: 12352209
• NACRES: NA.22
• MDL number: MFCD00037130

Properties

• Quality Level: 200
• product line: Novabiochem^®
• assay: ≥97.0% (acidimetric), ≥98% (TLC), ≥98.0% (HPLC)
• form: powder
• reaction suitability: reaction type: Fmoc solid-phase peptide synthesis
• manufacturer/tradename: Novabiochem^®
• mp: 133-136 °C
• application(s): peptide synthesis
• functional group: thiol
• storage temp.: 2-30°C
• SMILES string: S(C(C)(C)C)CC(NC(=O)OCC1c2c(cccc2)c3c1cccc3)C(=O)O
• InChI: 1S/C22H25NO4S/c1-22(2,3)28-13-19(20(24)25)23-21(26)27-12-18-16-10-6-4-8-14(16)15-9-5-7-11-17(15)18/h4-11,18-19H,12-13H2,1-3H3,(H,23,26)(H,24,25)
• InChI key: IXAYZHCPEYTWHW-UHFFFAOYSA-N

Description

General description

The side-chain tBu group is stable to TFA and iodine oxidation. Treatment with MeSiCl₃/PhSOPh removes t-Bu and cyclizes in one step without scrambling existing disulphide bonds. Removed with Hg(II) to give cysteinyl peptides.

Associated Protocols and Technical Articles
Cleavage and Deprotection Protocols for Fmoc SPPS
Fmoc SPPS of Cysteine-Containing Peptides

Literature references

^[1] S. N. McCurdy (1989) Pept. Res., 2, 147.

Analysis Note

Colour (visual): white to slight yellow to beige
Appearance of substance (visual): powder
Identity (IR): passes test
Enantiomeric purity: ≥ 99.5 % (a/a)
Purity (TLC(011A)): ≥ 98 %
Purity (TLC(0811)): ≥ 98 %
Assay (HPLC, area%): ≥ 98.0 % (a/a)
Solubility (1 mmole in 2 ml DMF): clearly soluble
Assay (acidimetric): ≥ 97.0 %
Water (K. F.): ≤ 1.00 %

To see the solvent systems used for TLC of Novabiochem^® products please click here.

Other Notes

Replaces: 04-12-1016

Legal Information

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

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable