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8.52008
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
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Quality Level
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)
SMILES string
S(C[C@H](NC(=O)OCC4c5c(cccc5)c6c4cccc6)C(=O)[O-])C(c3ccccc3)(c2ccccc2)c1ccccc1
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
1 of 4
This Item | 47695 | 8.52266 | 8.52143 |
|---|---|---|---|
| form powder | form - | form powder | form powder |
| functional group thiol | functional group Fmoc | functional group thiol | functional group thiol |
| assay ≥98% (TLC), ≥99.0% (HPLC), ≥98.0% (acidimetric) | assay ≥95.0% (sum of enantiomers, HPLC) | assay ≥95.0% (HPLC), ≥97% (TLC) | assay ≥90.0% (acidimetric), ≥98% (TLC), ≥99.0% (HPLC) |
| product line Novabiochem® | product line - | product line Novabiochem® | product line Novabiochem® |
| storage temp. −20°C (−15°C to −25°C) | storage temp. 2-8°C | storage temp. 15-25°C | storage temp. 15-25°C |
| mp 164-175 °C | mp 170-173 °C (lit.) | mp - | mp 168-173 °C |
General description
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).
Analysis Note
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.
Other Notes
Legal Information
Storage Class Code
11 - Combustible Solids
WGK
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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Protocols
Overcome challenges in synthesis and disulfide bond formation with protocols for Fmoc solid-phase peptide synthesis of peptides with cysteine and methionine.
Related Content
Discover 20 proteinogenic Novabiochem® Fmoc-amino acids, featuring enhanced specifications designed to optimize yields in peptide synthesis.
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How is shipping temperature determined? And how is it related to the product storage temperature?
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Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf
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