8.52338
Fmoc-thioproline
Novabiochem®
Synonym(s):
Fmoc-thioproline, Fmoc-thiaproline,Fmoc-thiazolidine-4-carboxylic acid
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About This Item
Empirical Formula (Hill Notation):
C19H17N4S
CAS Number:
Molecular Weight:
333.43
MDL number:
UNSPSC Code:
12352209
NACRES:
NA.22
Quality Level
product line
Novabiochem®
assay
≥98% (TLC), ≥99.0% (HPLC)
form
powder
reaction suitability
reaction type: Fmoc solid-phase peptide synthesis
manufacturer/tradename
Novabiochem®
application(s)
peptide synthesis
functional group
Fmoc
storage temp.
15-25°C
SMILES string
S1CN([C@@H](C1)C(=O)O)C(=O)OCC2c3c(cccc3)c4c2cccc4
InChI
1S/C19H17NO4S/c21-18(22)17-10-25-11-20(17)19(23)24-9-16-14-7-3-1-5-12(14)13-6-2-4-8-15(13)16/h1-8,16-17H,9-11H2,(H,21,22)/t17-/m0/s1
InChI key
HUWNZLPLVVGCMO-KRWDZBQOSA-N
General description
A building block for the introduction of thiaproline (Thz) during Fmoc SPPS. Thz has been employed as a masked cysteine residue to prevent self-ligation during native chemical ligation reactions (NCL) of peptide thioesters bearing an N-terminal Cys residue [6]. Once ligation is complete, the N-terminal Cys residue of the resultant peptide is unmasked by ring-opening the Thz residue by treatment with methoxyamine, thereby enabling its subsequent ligation to another peptide thioester fragment.
Associated Protocols and Technical Articles
Cleavage and Deprotection Protocols for Fmoc SPPS
Literature references
[1] M. Villain, et al. in ′Peptides: The wave of the future, Proc. Second Int.& 17th American Peptide Symposium′, M. Lebl & R A. Houghten (Eds), American peptide Society, 2001, pp. 107.
Associated Protocols and Technical Articles
Cleavage and Deprotection Protocols for Fmoc SPPS
Literature references
[1] M. Villain, et al. in ′Peptides: The wave of the future, Proc. Second Int.& 17th American Peptide Symposium′, M. Lebl & R A. Houghten (Eds), American peptide Society, 2001, pp. 107.
Analysis Note
Colour (visual): white to slight yellow to beige
Appearance of substance (visual): powder
Identity (IR): passes test
Enantiomeric purity: ≥ 99.5 % (a/a)
Purity (TLC(011A)): ≥ 98 %
Assay (HPLC, area%): ≥ 99.0 % (a/a)
Solubility (1 mmole in 2 ml DMF): clearly soluble
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)
Purity (TLC(011A)): ≥ 98 %
Assay (HPLC, area%): ≥ 99.0 % (a/a)
Solubility (1 mmole in 2 ml DMF): clearly soluble
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
11 - Combustible Solids
wgk
WGK 3
Regulatory Information
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Global Trade Item Number
| SKU | GTIN |
|---|---|
| 8523380005 | 04027269252649 |
| 8523380001 | 04027269252632 |
| 8523380025 | 04027269252656 |