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8.52031

Sigma-Aldrich

Fmoc-Cys(Mmt)-OH

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

Synonym(s):

Fmoc-Cys(Mmt)-OH, N-α-Fmoc-S-p-methoxytrityl-L-cysteine

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About This Item

Empirical Formula (Hill Notation):
C38H33NO5S
CAS Number:
Molecular Weight:
615.74
MDL number:
UNSPSC Code:
12352209
NACRES:
NA.22

product name

Fmoc-Cys(Mmt)-OH, Novabiochem®

Quality Level

product line

Novabiochem®

assay

≥85.0% (acidimetric)
≥98.0% (HPLC)
≥99% (TLC)

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/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

InChI key

LOBUWFUSGOYXQX-DHUJRADRSA-N

General description

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.

Application

  • 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

Analysis Note

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.

Legal Information

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

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Articles

Novabiochem® offers orthogonally protected amino acids for peptide synthesis, including cyclic and branched peptides.

Protocols

Overcome challenges in synthesis and disulfide bond formation with protocols for Fmoc solid-phase peptide synthesis of peptides with cysteine and methionine.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

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