8.52417

Fmoc-Cys(Dpm)-OH

Novabiochem^®

• Synonym(s): Fmoc-Cys(Dpm)-OH, N-α-Fmoc-S-diphenylmethyl-L-cysteine
• Empirical Formula (Hill Notation): C₃₁H₂₇NO₄S
• CAS Number: 247595-29-5
• Molecular Weight: 509.62
• UNSPSC Code: 12352209
• NACRES: NA.22

Properties

• Quality Level: 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
• InChI: 1S/C31H27NO4S/c33-30(34)28(20-37-29(21-11-3-1-4-12-21)22-13-5-2-6-14-22)32-31(35)36-19-27-25-17-9-7-15-23(25)24-16-8-10-18-26(24)27/h1-18,27-29H,19-20H2,(H,32,35)(H,33,34)/t28-/m0/s1
• InChI key: IVPLDYIPIHKRET-NDEPHWFRSA-N

Description

General description

The Dpm group has increased stability compared to Trt, enabling selective removal of Mtt groups on the solid phase with dilute TFA without loss of Dpm groups. Furthermore, the Dpm group is removed by treatment with 95% TFA cleavage cocktails. Racemization during carboxyl activation is lower with this derivative than with Fmoc-Cys(Trt)-OH.

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

Literature references

^[1] H. Hibino, et al. (2014) J. Pept. Sci., 20, 30.
^[2] M. Góngora-Benítez, et al. (2012) Org.Lett., 14, 5472.

Analysis Note

Colour (visual): white to off white
Appearance of substance (visual): powder
Identity (IR): passes test
Enantiomeric purity: ≥ 99.5 % (a/a)
Purity (HPLC): ≥ 98.0 % (a/a)
Purity (TLC(011A)): ≥ 98 %
Purity (TLC(0811)): ≥ 98 %
Solubility (1 mmole in 2 ml DMF): clearly soluble
Ethyl acetate (HS-GC): ≤ 0.5 %
Acetate (IC): ≤ 0.1 %

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_germany: WGK 1
• flash_point_f: Not applicable
• flash_point_c: Not applicable