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Sigma-Aldrich

Fmoc-Cys(tButhio)-OH

Novabiochem®

Synonym(s):

Fmoc-Cys(tButhio)-OH, N-α-Fmoc-S-t.-butylthio-L-cysteine

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About This Item

Empirical Formula (Hill Notation):
C22H25NO4S2
CAS Number:
73724-43-3
Molecular Weight:
431.57
MDL number:
MFCD00042617
UNSPSC Code:
12352209
EC Index Number:
277-574-6
NACRES:
NA.22

Quality Level

200

product line

Novabiochem®

Assay

≥95.0% (acidimetric)
≥97.0% (HPLC)
≥98% (TLC)

form

powder

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

manufacturer/tradename

Novabiochem®

mp

69-79 °C

application(s)

peptide synthesis

functional group

thiol

storage temp.

15-25°C

InChI

1S/C22H25NO4S2/c1-22(2,3)29-28-13-19(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)/t19-/m0/s1

InChI key

ZDUMTHLUTJOUML-IBGZPJMESA-N

Related Categories

General description

Building block for introduction of cysteinyl residues by Fmoc SPPS. The t-Buthio group can be selectively removed using thiols [1] or tributylphosphine[2,3]. This protecting group is stable to TFA if thiol scavengers are not used.

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

Literature references

[1] U. Weber & P. Hartter (1970) Hoppe-Seyler′s Z. Physiol. Chem., 351, 1384.
[2] U. T. Ruegg & H. G. Gattner (1975) Hoppe-Seyler′s Z. Physiol. Chem., 356, 1527.
[3] N. J. C. Beekman, et al. (1997) J. Peptide Res., 50, 357.

Linkage

Replaces: 04-12-1041

Analysis Note

Color (visual): white to slight yellow to beige
Appearance of substance (visual): powder
Identity (IR): passes test
Purity (TLC(011B)): ≥ 98 %
Purity (TLC(0811)): ≥ 98 %
Enantiomeric purity: ≥ 99.5 % (a/a)
Assay (HPLC, area%): ≥ 97.0 % (a/a)
Solubility (1 mmole in 2 ml DMF): clearly soluble
Assay (acidimetric): ≥ 95.0 %
Water (K. F.): ≤ 2.00 %

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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Articles

Selecting Orthogonal Building Blocks

Novabiochem® product range has one of the largest collections of orthogonally and quasi-orthogonally protected tri-functional amino acids. These derivatives are useful tools for the synthesis of cyclic and branched peptides and peptides carrying side-chain modifications.

Protocols

Selecting Orthogonal Building Blocks

Novabiochem® product range has one of the largest collections of orthogonally and quasi-orthogonally protected tri-functional amino acids. These derivatives are useful tools for the synthesis of cyclic and branched peptides and peptides carrying side-chain modifications

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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