8.52031

Fmoc-Cys(Mmt)-OH

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

• Sinonimo/i: Fmoc-Cys(Mmt)-OH, N-α-Fmoc-S-p-methoxytrityl-L-cysteine
• Formula empirica (notazione di Hill): C₃₈H₃₃NO₅S
• Numero CAS: 177582-21-7
• Peso molecolare: 615.74
• Numero MDL: MFCD00270541
• Codice UNSPSC: 12352209
• NACRES: NA.22

Proprietà

• product name: Fmoc-Cys(Mmt)-OH, Novabiochem^®
• Livello qualitativo: 200
• Nome Commerciale: Novabiochem^®
• Saggio: ≥85.0% (acidimetric); ≥98.0% (HPLC); ≥99% (TLC)
• Forma fisica: powder
• Impiego in reazioni chimiche: reaction type: Fmoc solid-phase peptide synthesis
• Produttore/marchio commerciale: Novabiochem^®
• applicazioni: peptide synthesis
• Gruppo funzionale: thiol
• Temperatura di conservazione: 15-25°C
• 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; LOBUWFUSGOYXQX-DHUJRADRSA-N

Descrizione

Descrizione generale

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.

Applicazioni

• 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).

Linkage

Replaces: 04-12-1061

Risultati analitici

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.

Note legali

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

Informazioni sulla sicurezza

• Codice della classe di stoccaggio: 11 - Combustible Solids
• Classe di pericolosità dell'acqua (WGK): WGK 3
• Punto d’infiammabilità (°F): Not applicable
• Punto d’infiammabilità (°C): Not applicable