Sigma-Aldrich Fmoc-Thioproline Novabioch

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

Related Categories

Amino Acids, Resins & Reagents for Peptide Synthesis

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

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