903736

Fmoc-Ser(PO(NHPr)₂)-OH

≥95%

• Sinonimo/i: Fmoc-Ser(PO(NH-CH₂-CH₂-CH₃)₂)-OH, Fmoc-protected phosphorylated serine amino acid building block, N-(((9H-Fluoren-9-yl)methoxy)carbonyl)-O-(bis(propylamino)phosphoryl)-L-serine
• Formula empirica (notazione di Hill): C₂₄H₃₂N₃O₆P
• Numero CAS: 216061-08-4
• Peso molecolare: 489.50
• Codice UNSPSC: 12352209

Proprietà

• Saggio: ≥95%
• Stato: solid
• Impiego in reazioni chimiche: reaction type: Fmoc solid-phase peptide synthesis
• applicazioni: peptide synthesis
• Gruppo funzionale: Fmoc
• Temperatura di conservazione: −20°C

Descrizione

Applicazioni

In the standard derivatives for introduction of phosphoserine and phosphothreonine in Fmoc SPPS, the phosphate side chain is monoprotected as a benzyl ester. The phosphate group therefore retains an acidic proton, which helps prevent beta-elimination of the phosphate group during the piperidine treatment utilized to remove the Fmoc protecting group in Fmoc SPPS. However, the acidic phosphate group can promote premature cleavage of peptides from hyperacid-labile resins such as 2-chlorotrityl resins. Furthermore, the phosphate forms piperidine salts during peptide assembly; these salts react with the activated Fmoc-amino acid during the coupling reaction, consuming valuable reagents and reducing their concentration.

Fmoc-Ser(PO(NPr)₂)OH and Fmoc-Thr(PO(NPr)₂)-OH are novel derivatives for introduction of phosphoserine and phosphothreonine in Fmoc SPPS, in which the phosphate group is fully protected as a phosphodiamidate. Model studies indicate these compounds, lacking the residual acidic proton, do not appear to suffer the aforementioned drawbacks of the currently employed monobenzylphosphate derivatives. Removal of the dimethyamino groups are removed during the course of the normal TFA cleavage and deprotection reaction.

Altre note

Novabiochem^® Publication Index

Note legali

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

Informazioni sulla sicurezza

• Codice della classe di stoccaggio: 11 - Combustible Solids
• Classe di pericolosità dell'acqua (WGK): WGK 3
• Punto d’infiammabilità (°F): Not applicable
• Punto d’infiammabilità (°C): Not applicable