8.52338

Fmoc-thioproline

Novabiochem^®

• Synonym(s): Fmoc-thioproline, Fmoc-thiaproline,Fmoc-thiazolidine-4-carboxylic acid
• Empirical Formula (Hill Notation): C₁₉H₁₇N₄S
• CAS Number: 133054-21-4
• Molecular Weight: 333.43
• UNSPSC Code: 12352209
• NACRES: NA.22

Properties

• Quality Level: 200
• 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
• 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

Description

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.

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.

Legal Information

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

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3