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8.52008

Sigma-Aldrich

Fmoc-Cys(Trt)-OH

Novabiochem®

Synonym(s):

Fmoc-Cys(Trt)-OH, N-α-Fmoc-S-trityl-L-cysteine

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About This Item

Empirical Formula (Hill Notation):
C37H31NO4S
CAS Number:
103213-32-7
Molecular Weight:
585.71
MDL number:
MFCD00038538
UNSPSC Code:
12352209

Quality Level

400

product line

Novabiochem®

assay

≥98% (TLC)
≥98.0% (acidimetric)
≥99.0% (HPLC)

form

powder

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

manufacturer/tradename

Novabiochem®

mp

164-175 °C

application(s)

peptide synthesis

functional group

thiol

storage temp.

−20°C (−15°C to −25°C)

InChI

1S/C37H31NO4S/c39-35(40)34(38-36(41)42-24-33-31-22-12-10-20-29(31)30-21-11-13-23-32(30)33)25-43-37(26-14-4-1-5-15-26,27-16-6-2-7-17-27)28-18-8-3-9-19-28/h1-23,33-34H,24-25H2,(H,38,41)(H,39,40)/p-1/t34-/m0/s1

InChI key

KLBPUVPNPAJWHZ-UMSFTDKQSA-M

Related Categories

General description

High purity Fmoc-protected amino acid for research and process production of peptides, with very low levels of dipeptide, free-amino acids and acetic acid impurities. The standard derivative for Fmoc SPPS of peptides containing Cys [1]. The Trt group is removed with 95% TFA containing 1-5% TIS. Ideally, this derivative should be introduced using the symmetrical anhydride or DIPCDI/HOBt activation [2,3] to minimize enantiomerization. If activation with uronium or phosphonium reagents, such as HBTU or PyBOP®, is to be employed, it is strongly recommended that collidine is used as the base [4], as this has been shown to significantly reduce loss of optical integrity during coupling.


Associated Protocols and Technical Articles
Fmoc-amino acids for Peptide Production
Cleavage and Deprotection Protocols for Fmoc SPPS
Fmoc SPPS of Cysteine-Containing Peptides

Literature references

[1] S. N. McCurdy (1989) Pept. Res., 2, 147.
[2] T. Kaiser, et al. (1996) Tetrahedron Lett., 37, 1187.
[3] Y. X. Han, et al. (1997) J. Org. Chem., 62, 4307.
[4] Y. N. Angell (2002) J. Peptide Res., 5, 292.

Application

  • On-resin synthesis of cyclic peptides via tandem N-to-S acyl migration and intramolecular thiol additive-free native chemical ligation: Discusses the use of Fmoc-Cys(Trt)-OH in the synthesis of cyclic peptides, highlighting the efficiency of the resin synthesis method. (Serra et al., 2020).
  • Selective Bi‐directional Amide Bond Cleavage of N‐Methylcysteinyl Peptide: The study utilized Fmoc-Cys(Trt)-OH in exploring selective bi-directional amide bond cleavage in peptides, providing insights into controlled peptide modification. (Qiu et al., 2014).

Linkage

Replaces: 04-12-1018

Analysis Note

Colour (visual): white to off white
Appearance of substance (visual): powder
Colour index (0,5 M in DMF): ≤ 150 Hazen
Identity (IR): passes test
Enantiomeric purity: ≥ 99.5 % (a/a)
Purity (HPLC): ≥ 99.0 % (a/a)
Fmoc-ß-Ala-OH (HPLC): ≤ 0.1 % (a/a)
Fmoc-ß-Ala-Cys (Trt) -OH (HPLC): ≤ 0.1 % (a/a)
Fmoc-Cys(Trt)-Cys(Trt)-OH (HPLC): ≤ 0.1 % (a/a)
Fmoc-Cys-OH (HPLC): ≤ 0.1 % (a/a)
Assay free amino acid (HPLC): ≤ 0.2 %
Purity (TLC(011A)): ≥ 98 %
Purity (TLC(0811)): ≥ 98 %
Solubility (1 mmole in 2 ml DMF): clearly soluble
Assay (acidimetric): ≥ 98.0 %
Water (K. F.): ≤ 2.0 %
Ethyl acetate (HS-GC): ≤ 0.5 %
Acetate (IC): ≤ 0.02 %

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

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Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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