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8.52006

Sigma-Aldrich

Fmoc-Cys(Acm)-OH

≥99.0% (HPLC), for peptide synthesis, Novabiochem®

Synonym(s):

Fmoc-Cys(Acm)-OH, N-α-Fmoc-S-acetamidomethyl-L-cysteine

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About This Item

Empirical Formula (Hill Notation):
C21H22N2O5S
CAS Number:
Molecular Weight:
414.47
MDL number:
UNSPSC Code:
12352209
NACRES:
NA.22

product name

Fmoc-Cys(Acm)-OH, Novabiochem®

Quality Level

product line

Novabiochem®

Assay

≥96.0% (acidimetric)
≥98% (TLC)
≥99.0% (HPLC)

form

powder

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

manufacturer/tradename

Novabiochem®

mp

147-150 °C

application(s)

peptide synthesis

functional group

thiol

storage temp.

2-30°C

InChI

1S/C21H22N2O5S/c1-13(24)22-12-29-11-19(20(25)26)23-21(27)28-10-18-16-8-4-2-6-14(16)15-7-3-5-9-17(15)18/h2-9,18-19H,10-12H2,1H3,(H,22,24)(H,23,27)(H,25,26)/t19-/m0/s1

InChI key

CSMYOORPUGPKAP-IBGZPJMESA-N

General description

The side-chain Acm group is stable to TFA but can be removed with Hg(II) [1] or Ag(I) [2] to give cysteinyl peptides, or oxidatively with Tl(III) [3] or I2 [4] to generate cystinyl peptides.

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

Literature references

[1] D. F. Veber, et al. (1972) J. Am. Chem. Soc., 94, 5456.
[2] M. Yoshida, et al. (1990) Chem. Pharm. Bull., 38, 273.
[3] N. Fujii, et al. (1987) Chem. Pharm. Bull., 36, 2339.
[4] B. Kamber, et al. (1980) Helv. Chim. Acta, 63, 899.

Linkage

Replaces: 04-12-1014

Analysis Note

Color (visual): white to slight yellow to beige
Appearance of substance (visual): powder
Identity (IR): passes test
Enantiomeric purity: ≥ 99.5 % (a/a)
Purity (TLC(011B)): ≥ 98 %
Purity (TLC(0811)): ≥ 98 %
Assay (HPLC, area%): ≥ 99.0 % (a/a)
Solubility (25 mmole in 50 ml DMF): clearly soluble
UV/VIS (E(450 bis 600 nm)): ≤ 50 mAU
Assay (acidimetric): ≥ 96.0 %
Water (K. F.): ≤ 5.00 %

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

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

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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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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