8.52346

Fmoc-Sec(pMeOBzl)-OH

≥98.0% (HPLC), for peptide synthesis, Novabiochem^®

• Synonyme(s) : Fmoc-Sec(pMeOBzl)-OH, Fmoc-Sec(Mob)-OH,Fmoc-S-4-methoxybenzyl selenocysteine
• Formule empirique (notation de Hill): C₂₆H₂₅NO₅Se
• Numéro CAS: 150308-80-8
• Poids moléculaire : 510.44
• Code UNSPSC : 12352209
• Nomenclature NACRES : NA.22

Propriétés

• product name: Fmoc-Sec(pMeOBzl)-OH, Novabiochem^®
• Niveau de qualité: 200
• Gamme de produits: Novabiochem^®
• Pureté: ≥98% (TLC); ≥98.0% (HPLC)
• Forme: powder
• Capacité de réaction: reaction type: Fmoc solid-phase peptide synthesis
• Fabricant/nom de marque: Novabiochem^®
• Application(s): peptide synthesis
• Groupe fonctionnel: Fmoc
• Température de stockage: 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
• Clé InChI: XCPAYIZRJRMXBI-DEOSSOPVSA-N

Description

Description générale

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 ^[3]. 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)^[2] or TFA-water-DCM-TIS (89:5:51) at 4 °C ^[3]. 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

^[1] T. Koide, et al. (1993) Chem. Pharm. Bull., 41, 502.
^[2] T. Koide, et al. (1993) Chem. Pharm. Bull., 41, 1596.
^[3] D. Besse & L. Moroder (1997) J. Peptide Sci., 3, 442.

Remarque sur l'analyse

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.

Informations légales

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

Informations sur la sécurité

• Pictogrammes: GHS06,GHS08,GHS09
• Mention d'avertissement: Danger
• Mentions de danger: H301 + H331 - H315 - H335 - H373 - H410
• Conseils de prudence: P260 - P273 - P301 + P310 - P302 + P352 - P304 + P340 + P311 - P314
• Classification des risques: Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Skin Irrit. 2 - STOT RE 2 - STOT SE 3
• Organes cibles: Respiratory system
• Code de la classe de stockage: 6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• Classe de danger pour l'eau (WGK): WGK 3
• Point d'éclair (°F): Not applicable
• Point d'éclair (°C): Not applicable