Sigma-Aldrich Fmoc-Val-Ser(Psime,Mepro)

Quality Level

200

Product Line

Novabiochem^®

Assay

≥97% (TLC)
≥97.0% (HPLC)

Form

powder

Reaction Suitability

reaction type: Fmoc solid-phase peptide synthesis

Manufacturer/Tradename

Novabiochem^®

Application(S)

peptide synthesis

Functional Group

hydroxyl

Storage Temp.

2-8°C

Inchi

1S/C26H30N2O6/c1-15(2)22(23(29)28-21(24(30)31)14-34-26(28,3)4)27-25(32)33-13-20-18-11-7-5-9-16(18)17-10-6-8-12-19(17)20/h5-12,15,20-22H,13-14H2,1-4H3,(H,27,32)(H,30,31)/t21-,22-/m0/s1

Related Categories

Amino Acids, Resins & Reagents for Peptide Synthesis

General Description

This pseudoproline dipeptide is undoubtedly the most effective and simplest to use tool for overcoming aggregation and enhancing peptide quality in Fmoc SPPS for peptide containing the Val-Ser dipeptide motif. It consists of a dipeptide in which the serine residue has been reversibly protected as a structure-breaking proline-like TFA-labile oxazolidine. The reason the pseudoproline residue is introduced as a dipeptide is because it avoids the need to acylate the hindered oxazolidine nitrogen. This has the added advantage of extending the peptide chain by two residues in one step. The serine residue is regenerated during the normal TFA-mediated cleavage reaction.

Associated Protocols and Technical Articles
Cleavage and Deprotection Protocols for Fmoc SPPS
Overcoming Aggregation in Fmoc SPPS

Linkage

Replaces: 05-20-1001

Analysis Note

Color (visual): white to slight yellow to beige
Appearance of substance (visual): powder
Identity (IR): passes test
Optical rotation α 25/D (c=1 in CH₂Cl₂): -50.0 - -43.0 °
Purity (TLC(157A)): ≥ 97 %
Purity (TLC(CMA2)): ≥ 97 %
Assay (HPLC, area%): ≥ 97.0 % (a/a)
Single impurities (HPLC, area%): ≤ 1.00 % (a/a)
Acetate (IC): ≤ 0.1 %
Ethyl acetate (HS-GC): ≤ 2.0 %

To see the solvent systems used for TLC of Novabiochem^®products please click here.Novabiochem is a registered trademark of Merck KGaA, Darmstadt, Germany