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Merck
CN

8.52031

Fmoc-Cys(Mmt)-OH

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

别名:

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

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关于此项目

经验公式（希尔记法）:
C38H33NO5S
化学文摘社编号:
177582-21-7
分子量:
615.74
UNSPSC Code:
12352209
NACRES:
NA.22
MDL number:
MFCD00270541

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产品名称

Fmoc-Cys(Mmt)-OH, Novabiochem®

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

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

Quality Level

200

相关类别

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.

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).

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.

Other Notes

Replaces: 04-12-1061

Legal Information

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

存储类别

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

法规信息

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商品

Selecting Orthogonal Building Blocks

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

实验方案

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.

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