Sigma-Aldrich Fmoc-Sec(Pmeobzl)-Oh Novab

Quality Level

200

Product Line

Novabiochem^®

Assay

≥98% (TLC)
≥98.0% (HPLC)

Form

powder

Reaction Suitability

reaction type: Fmoc solid-phase peptide synthesis

Manufacturer/Tradename

Novabiochem^®

Application(S)

peptide synthesis

Functional Group

Fmoc

Storage Temp.

2-8°C

Inchi

1S/C26H25NO5Se/c1-31-18-12-10-17(11-13-18)15-33-16-24(25(28)29)27-26(30)32-14-23-21-8-4-2-6-19(21)20-7-3-5-9-22(20)23/h2-13,23-24H,14-16H2,1H3,(H,27,30)(H,28,29)/t24-/m0/s1

Related Categories

Amino Acids, Resins & Reagents for Peptide Synthesis

General Description

Building block for the introduction of selenocysteine during Fmoc SPPS ^[1,2,3] . Selenocysteine derivatives can undergo enantiomerization during coupling and can form dehydroalanine and β-piperidinylalanine containing side products during subsequent chain elongation . Therefore, activation methods, such as HBTU or PyBOP which involve the addition of a tertiary, base should be avoided for addition of the Sec and all subsequent residues. Cleavage and side-chain deprotection of Sec-containing peptides can be effected using TFA-M-cresol-thioanisole-EDT-water (80:5:5:5:5) or TFA-water-DCM-TIS (89:5:51) at 4 °C . As the Se-pMeOBzl bond is stable to TFA, these methods result in the formation of the corresponding Sev(pMeOBzl) peptide. Peptides containing two Sec(pMeOBzl) residues can be oxidized directly to the corresponding selenocystinyl peptides by treatment with 5-10% DMSO in TFA ^[1-3].

Associated Protocols and Technical Articles
Cleavage and Deprotection Protocols for Fmoc SPPS

Literature references

T. Koide, et Al. (1993)Chem. Pharm. Bull.,41, 502.
T. Koide, et Al. (1993)Chem. Pharm. Bull.,41, 1596.
D. Besse & L. Moroder (1997)J. Peptide Sci.,3, 442.

Analysis Note

Color (visual): white to yellow to beige
Appearance of substance (visual): powder
Identity (IR): passes test
Enantiomeric purity: ≥ 99.5 % (a/a)
Purity (TLC(157A)): ≥ 98 %
Assay (HPLC, area%): ≥ 98.0 % (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, GermanyGHS06,GHS08,GHS09H301 + H331 - H315 - H335 - H373 - H410P260 - P273 - P301 + P310 - P302 + P352 - P304 + P340 + P311 - P314