8.52373

Fmoc-Cys(STmp)-OH

for peptide synthesis, Novabiochem^®

• Sinónimos: Fmoc-Cys(STmp)-OH, N-α-Fmoc-S-2,4,6-trimethoxyphenylthio-L-cysteine
• Fórmula empírica (notación de Hill): C₂₇H₂₇NO₇S₂
• Número de CAS: 1403834-74-1
• Peso molecular: 541.64
• Número MDL: MFCD27957369
• Código UNSPSC: 12352209
• NACRES: NA.22

Propiedades

• Nombre del producto: Fmoc-Cys(STmp)-OH, Novabiochem^®
• Nivel de calidad: 200
• Línea del producto: Novabiochem^®
• Formulario: powder
• idoneidad de la reacción: reaction type: Fmoc solid-phase peptide synthesis
• fabricante / nombre comercial: Novabiochem^®
• aplicaciones: peptide synthesis
• grupo funcional: thiol
• temp. de almacenamiento: 15-25°C
• cadena SMILES: 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
• Clave InChI: GADCBXMSWHDNAU-QFIPXVFZSA-N

Descripción

Descripción general

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.

Aplicación

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.

Nota de análisis

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.

Información legal

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

Información de seguridad

• Código de clase de almacenamiento: 11 - Combustible Solids
• Clase de riesgo para el agua (WGK): WGK 1
• Punto de inflamabilidad (°F): Not applicable
• Punto de inflamabilidad (°C): Not applicable