8.52346

Fmoc-Sec(pMeOBzl)-OH

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

• Synonym(s): Fmoc-Sec(pMeOBzl)-OH, Fmoc-Sec(Mob)-OH,Fmoc-S-4-methoxybenzyl selenocysteine
• Empirical Formula (Hill Notation): C₂₆H₂₅NO₅Se
• CAS Number: 150308-80-8
• Molecular Weight: 510.44
• UNSPSC Code: 12352209
• NACRES: NA.22

Properties

• product name: Fmoc-Sec(pMeOBzl)-OH, Novabiochem^®
• 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
• InChI key: XCPAYIZRJRMXBI-DEOSSOPVSA-N

Description

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 ^[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.

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.

Legal Information

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

Safety Information

• Pictograms: GHS06,GHS08,GHS09
• Signal Word: Danger
• Hazard Statements: H301 + H331 - H315 - H335 - H373 - H410
• Precautionary Statements: P260 - P273 - P301 + P310 - P302 + P352 - P304 + P340 + P311 - P314
• Hazard Classifications: Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Skin Irrit. 2 - STOT RE 2 - STOT SE 3
• Target Organs: Respiratory system
• Storage Class Code: 6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable