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8.52031

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:
177582-21-7
Molecular Weight:
615.74
UNSPSC Code:
12352209
NACRES:
NA.22
MDL number:
MFCD00270541
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Product Name

Fmoc-Cys(Mmt)-OH, Novabiochem®

Quality Level

200

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

SMILES string

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

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).

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.

Other Notes

Replaces: 04-12-1061

Legal Information

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

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Protocols

Protocols for the Fmoc SPPS of Cysteine-Containing Peptides

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

Articles

Selecting Orthogonal Building Blocks

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

Global Trade Item Number

SKUGTIN
852031002504027269086251
852031000504027269086244
852031000104027269086237