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8.52007

Fmoc-Cys(tBu)-OH

Novabiochem®

Synonym(s):

Fmoc-Cys(tBu)-OH, N-α-Fmoc-S-t.-butyl-L-cysteine

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About This Item

Empirical Formula (Hill Notation):
C22H25NO4S
CAS Number:
67436-13-9
Molecular Weight:
399.50
UNSPSC Code:
12352209
NACRES:
NA.22
MDL number:
MFCD00037130
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Quality Level

200

product line

Novabiochem®

assay

≥98.0% (HPLC), ≥97.0% (acidimetric), ≥98% (TLC)

form

powder

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

manufacturer/tradename

Novabiochem®

mp

133-136 °C

application(s)

peptide synthesis

functional group

thiol

storage temp.

2-30°C

SMILES string

S(C(C)(C)C)CC(NC(=O)OCC1c2c(cccc2)c3c1cccc3)C(=O)O

InChI

1S/C22H25NO4S/c1-22(2,3)28-13-19(20(24)25)23-21(26)27-12-18-16-10-6-4-8-14(16)15-9-5-7-11-17(15)18/h4-11,18-19H,12-13H2,1-3H3,(H,23,26)(H,24,25)

InChI key

IXAYZHCPEYTWHW-UHFFFAOYSA-N

General description

The side-chain tBu group is stable to TFA and iodine oxidation. Treatment with MeSiCl3/PhSOPh removes t-Bu and cyclizes in one step without scrambling existing disulphide bonds. Removed with Hg(II) to give cysteinyl peptides.

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

Literature references

[1] S. N. McCurdy (1989) Pept. Res., 2, 147.

Analysis Note

Colour (visual): white to slight yellow to beige
Appearance of substance (visual): powder
Identity (IR): passes test
Enantiomeric purity: ≥ 99.5 % (a/a)
Purity (TLC(011A)): ≥ 98 %
Purity (TLC(0811)): ≥ 98 %
Assay (HPLC, area%): ≥ 98.0 % (a/a)
Solubility (1 mmole in 2 ml DMF): clearly soluble
Assay (acidimetric): ≥ 97.0 %
Water (K. F.): ≤ 1.00 %

To see the solvent systems used for TLC of Novabiochem® products please click here.

Other Notes

Replaces: 04-12-1016

Legal Information

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

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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.

Global Trade Item Number

SKUGTIN
852007010004027269084745
852007002504027269084738