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903736

Sigma-Aldrich

Fmoc-Ser(PO(NHPr)2)-OH

≥95%

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C24H32N3O6P
CAS Number:
216061-08-4
Molecular Weight:
489.50
UNSPSC Code:
12352209

Assay

≥95%

form

solid

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

application(s)

peptide synthesis

functional group

Fmoc

storage temp.

−20°C

Application

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.

Other Notes

Novabiochem® Publication Index

Legal Information

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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