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8.52006

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:
86060-81-3
Molecular Weight:
414.47
UNSPSC Code:
12352209
NACRES:
NA.22
MDL number:
MFCD00038769
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Product Name

Fmoc-Cys(Acm)-OH, Novabiochem®

Quality Level

200

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

SMILES string

S(CNC(=O)C)C[C@H](NC(=O)OCC1c2c(cccc2)c3c1cccc3)C(=O)O

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.

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.

Other Notes

Replaces: 04-12-1014

Legal Information

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

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pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

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

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
852006000504027269084639
852006010004027269084653
852006002504027269084646