Fmoc-D-Thr[PO(OBzl)-OH]-OH

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Catalog Number
ACM175291562-1
Product Name
Fmoc-D-Thr[PO(OBzl)-OH]-OH
Structure
Structure
CAS
175291-56-2
Category
Amino Acids
Description
Fmoc-O-(benzylphospho)-L-threonine is a phosphopeptide derivative that is used in the synthesis of proteins and peptides. The compound is formed by attaching a benzylphosphonic acid group to the hydroxyl group of the threonine residue. This modification can enhance the stability and specificity of the peptide or protein towards its target. The Fmoc (fluorenylmethoxycarbonyl) group is a common protecting group used in peptide synthesis to prevent unwanted chemical reactions during the coupling of amino acids.
Synonyms
Fmoc-Thr(PO(OBzl)OH)-OH, N-α-Fmoc-O-benzyl-L-phosphothreonine, Fmoc-O-(benzylphospho)-L-threonine
IUPAC Name
(2S,3R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-[hydroxy(phenylmethoxy)phosphoryl]oxybutanoic acid
Molecular Weight
511.5
Molecular Formula
C26H26NO8P
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
Density
1.4±0.1 g/cm3
Application
Fmoc-O-(benzylphospho)-L-threonine has been widely used in scientific experiments to improve the stability and specificity of peptides and proteins towards their targets. The compound has been used in the synthesis of various bioactive peptides, such as antimicrobial peptides, and has shown potential for various biomedical applications.
Assay
≥90.0% (acidimetric)
≥98% (TLC)
≥98.0% (HPLC)
Exact Mass
511.139618
Form
powder
Functional Group
Fmoc
Impurities
Water (K. F.): ≤ 2.0 %
LogP
5.09
MDL Number
MFCD00797870
PSA
141.2
Quality Level
200
Refractive Index
1.615
Storage Temperature
15-25℃
Type
Unusual Amino Acids, Phosphorylated Amino Acids
WGK Germany
3
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