8.52373

Fmoc-Cys(STmp)-OH

for peptide synthesis, Novabiochem^®

• Synonym(s): Fmoc-Cys(STmp)-OH, N-α-Fmoc-S-2,4,6-trimethoxyphenylthio-L-cysteine
• Empirical Formula (Hill Notation): C₂₇H₂₇NO₇S₂
• CAS Number: 1403834-74-1
• Molecular Weight: 541.64
• MDL number: MFCD27957369
• UNSPSC Code: 12352209
• NACRES: NA.22

Properties

• Product Name: Fmoc-Cys(STmp)-OH, Novabiochem^®
• Quality Segment: 200
• product line: Novabiochem^®
• form: powder
• reaction suitability: reaction type: Fmoc solid-phase peptide synthesis
• manufacturer/tradename: Novabiochem^®
• application(s): peptide synthesis
• functional group: thiol
• storage temp.: 15-25°C
• SMILES string: S(Sc4c(cc(cc4OC)OC)OC)C[C@H](NC(=O)OCC1c2c(cccc2)c3c1cccc3)C(=O)O
• InChI: 1S/C27H27NO7S2/c1-32-16-12-23(33-2)25(24(13-16)34-3)37-36-15-22(26(29)30)28-27(31)35-14-21-19-10-6-4-8-17(19)18-9-5-7-11-20(18)21/h4-13,21-22H,14-15H2,1-3H3,(H,28,31)(H,29,30)/t22-/m0/s1
• InChI key: GADCBXMSWHDNAU-QFIPXVFZSA-N

Description

General description

Fmoc-Cys(STmp)-OH is a novel new tool for the regioselective synthesis of multiple disulfide bridged peptides by Fmoc SPPS. The STmp group is stable to piperidine but is extremely easy to remove by mild thiolysis. Albericio has reported removing four STmp groups on the solid phase with only three 5 minute treatments of 0.1 M N-methylmorpholine (NMM) in DMF containing 5% DTT.

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

Literature references:
^[1] T. M. Postma, et al. (2012) Org. Lett., 14, 5468.
^[2] T. M. Postma & F. Albericio (2013) Org. Lett., 15, 616.

Application

Applications of Fmoc-Cys(STmp)-OH:

• Synthesis of insulin analogs by regiospecific disulfide bond formation.
• A review on step-wise introduction of disulfide bonds.
• Synthesis of human insulin-like peptide 6.

Analysis Note

Color (visual): white to slight yellow to beige
Appearance of substance (visual): powder
Identity (IR): passes test
Enantiomeric purity: ≥ 99.5 % (a/a)
Assay (HPLC, area%): ≥ 94.0 % (a/a)
Purity (TLC(011A)): ≥ 98 %
Solubility (1 mmole in 2 ml DMF): clearly soluble
Ethyl acetate (HS-GC): ≤ 0.5 %
Acetate (IC): ≤ 0.05 %

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

Legal Information

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

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk: WGK 1
• flash_point_f: Not applicable
• flash_point_c: Not applicable