8.52031

Fmoc-Cys(Mmt)-OH

≥99% (TLC), for peptide synthesis, Novabiochem^®

• Sinónimos: Fmoc-Cys(Mmt)-OH, N-α-Fmoc-S-p-methoxytrityl-L-cysteine
• Fórmula empírica (notación de Hill): C₃₈H₃₃NO₅S
• Número de CAS: 177582-21-7
• Peso molecular: 615.74
• Número MDL: MFCD00270541
• Código UNSPSC: 12352209
• NACRES: NA.22

Propiedades

• Nombre del producto: Fmoc-Cys(Mmt)-OH, Novabiochem^®
• Nivel de calidad: 200
• Línea del producto: Novabiochem^®
• Ensayo: ≥85.0% (acidimetric); ≥98.0% (HPLC); ≥99% (TLC)
• 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(C[C@H](NC(=O)OCC4c5c(cccc5)c6c4cccc6)C(=O)O)C(c3ccc(cc3)OC)(c2ccccc2)c1ccccc1
• InChI: 1S/C38H33NO5S/c1-43-29-22-20-28(21-23-29)38(26-12-4-2-5-13-26,27-14-6-3-7-15-27)45-25-35(36(40)41)39-37(42)44-24-34-32-18-10-8-16-30(32)31-17-9-11-19-33(31)34/h2-23,34-35H,24-25H2,1H3,(H,39,42)(H,40,41)/t35-/m0/s1
• Clave InChI: LOBUWFUSGOYXQX-DHUJRADRSA-N

Descripción

Descripción general

Building block for Fmoc SPPS which enables selective deprotection of cysteinyl thiol group on the solid phase. The Mmt group can be removed on the solid phase with 1% TFA in DCM containing 5% TIS ^[1,2,3,4]. Reference 4 describes a novel method for on-resin disulfide bond formation which uses Cys(Mmt) in combination with Cys(tBuS).

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

Literature references

^[1] K. Barlos, et al. in ′Peptides 1992, Proc. 22nd European Peptide Symposium′, C. H. Schneider & A. N. Eberle (Eds), ESCOM, Leiden, 1993, pp. 283.
^[2] C. Kellenberger, et al. (1995) Pept. Res., 8, 321.
^[3] K. Barlos, et al. (1996) Int. J. Peptide Protein Res., 47, 148.
^[4] A. K. Galande, et al. (2005) J. Comb. Chem., 7, 174.

Aplicación

• An Optimized Scalable Fully Automated Solid-Phase Microwave-Assisted cGMP-Ready Process for the Preparation of Eptifibatide: Details the use of Fmoc-Cys(Mmt)-OH in the synthesis of Eptifibatide, highlighting its role in a cGMP-ready process (Sabatino et al., 2020).

Ligadura / enlace

Replaces: 04-12-1061

Nota de análisis

Color (visual): white to slight yellow to beige
Appearance of substance (visual): powder
Identity (IR): passes test
Enantiomeric purity: ≥ 99.0 % (a/a)
Purity (TLC(011A)): ≥ 99 %
Purity (TLC(0811)): ≥ 99 %
Assay (HPLC, area%): ≥ 98.0 % (a/a)
Solubility (1 mmole in 2 ml DMF): clearly soluble
Assay (acidimetric): ≥ 85.0 %
Water (K. F.): ≤ 1.0 %

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 3
• Punto de inflamabilidad (°F): Not applicable
• Punto de inflamabilidad (°C): Not applicable