8.52373
Fmoc-Cys(STmp)-OH
for peptide synthesis, Novabiochem®
Synonym(s):
Fmoc-Cys(STmp)-OH, N-α-Fmoc-S-2,4,6-trimethoxyphenylthio-L-cysteine
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About This Item
Empirical Formula (Hill Notation):
C27H27NO7S2
CAS Number:
Molecular Weight:
541.64
UNSPSC Code:
12352209
NACRES:
NA.22
product name
Fmoc-Cys(STmp)-OH, Novabiochem®
Quality Level
product line
Novabiochem®
form
powder
reaction suitability
reaction type: Fmoc solid-phase peptide synthesis
manufacturer/tradename
Novabiochem®
application(s)
peptide synthesis
functional group
thiol
storage temp.
15-25°C
General description
Fmoc-Cys(STmp)-OH is a novel new tool for the regioselective synthesis of multiple disulfide bridged peptides by Fmoc SPPS. The STmp group is stable to piperidine but is extremely easy to remove by mild thiolysis. Albericio has reported removing four STmp groups on the solid phase with only three 5 minute treatments of 0.1 M N-methylmorpholine (NMM) in DMF containing 5% DTT.
Associated Protocols and Technical Articles
Cleavage and Deprotection Protocols for Fmoc SPPS
Fmoc SPPS of Cysteine-Containing Peptides
Literature references:
[1] T. M. Postma, et al. (2012) Org. Lett., 14, 5468.
[2] T. M. Postma & F. Albericio (2013) Org. Lett., 15, 616.
Associated Protocols and Technical Articles
Cleavage and Deprotection Protocols for Fmoc SPPS
Fmoc SPPS of Cysteine-Containing Peptides
Literature references:
[1] T. M. Postma, et al. (2012) Org. Lett., 14, 5468.
[2] T. M. Postma & F. Albericio (2013) Org. Lett., 15, 616.
Application
Applications of Fmoc-Cys(STmp)-OH:
- Synthesis of insulin analogs by regiospecific disulfide bond formation.
- A review on step-wise introduction of disulfide bonds.
- Synthesis of human insulin-like peptide 6.
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)
Assay (HPLC, area%): ≥ 94.0 % (a/a)
Purity (TLC(011A)): ≥ 98 %
Solubility (1 mmole in 2 ml DMF): clearly soluble
Ethyl acetate (HS-GC): ≤ 0.5 %
Acetate (IC): ≤ 0.05 %
To see the solvent systems used for TLC of Novabiochem® products please click here.
Appearance of substance (visual): powder
Identity (IR): passes test
Enantiomeric purity: ≥ 99.5 % (a/a)
Assay (HPLC, area%): ≥ 94.0 % (a/a)
Purity (TLC(011A)): ≥ 98 %
Solubility (1 mmole in 2 ml DMF): clearly soluble
Ethyl acetate (HS-GC): ≤ 0.5 %
Acetate (IC): ≤ 0.05 %
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 1
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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Find documentation for the products that you have recently purchased in the Document Library.
Trimethoxyphenylthio as a highly labile replacement for tert-butylthio cysteine protection in Fmoc solid phase synthesis
T. M. Postma, et al.,
Organic Letters, 14, 5468-5468 (2012)
Synthesis of Four-Disulfide Insulin Analogs via Sequential Disulfide Bond Formation
Fangzhou Wu, et al.
The Journal of Organic Chemistry, 82, 3506-3506 (2017)
Chemical Synthesis of Human Insulin-Like Peptide-6
Chemistry?A European Journal , 22, 9777-9777 (2016)
N-Chlorosuccinimide, an efficient reagent for on-resin disulfide formation in solid-phase peptide synthesis
T. M. Postma & F. Albericio
Organic Letters, 15, 616-616 (2013)
Stepwise Construction of Disulfides in Peptides
H Rongjun, et al.,
Chembiochem, 21, 1101-1101 (2020)
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