Specification
Description
An excellent building block for the preparation of D-phosphothreonine-containing peptides by Fmoc SPPS. This derivative can be introduced using standard activation methods, such as PyBOPand TBTU. The monoprotected phosphoserine residue once incorporated is stable to piperidine. Using this reagent, even peptides containing multiple phosphorylation sites can be prepared efficiently by standard Fmoc SPPS methods.
Synonyms
Fmoc-D-Thr(PO(OBzl)OH)-OH, N-α-Fmoc-O-benzyl-D-phosphothreonine
IUPAC Name
(2R,3S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-[hydroxy(phenylmethoxy)phosphoryl]oxybutanoic acid
Canonical SMILES
CC(C(C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13)OP(=O)(O)OCC4=CC=CC=C4
InChI
1S/C26H26NO8P/c1-17(35-36(31,32)34-15-18-9-3-2-4-10-18)24(25(28)29)27-26(30)33-16-23-21-13-7-5-11-19(21)20-12-6-8-14-22(20)23/h2-14,17,23-24H,15-16H2,1H3,(H,27,30)(H,28,29)(H,31,32)/t17-,24+/m0/s1
InChI Key
HOFDVXHILSPFNS-BXKMTCNYSA-N
Application
Peptide synthesis.
Assay
≥90.0% (acidimetric)
≥95.0% (HPLC)
≥97% (TLC)
Reaction Suitability
reaction type: Fmoc solid-phase peptide synthesis
Storage Temperature
15-25℃