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

CAS
937171-63-6
Catalog Number
ACM937171636
Category
Amino Acids
Molecular Weight
511.46
Molecular Formula
C26H26NO8P

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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
Density
1.4±0.1 g/cm3
Application
Peptide synthesis.
Assay
≥90.0% (acidimetric)
≥95.0% (HPLC)
≥97% (TLC)
Exact Mass
511.139618
Form
powder
Functional Group
Fmoc
LogP
5.09
PSA
141.2
Reaction Suitability
reaction type: Fmoc solid-phase peptide synthesis
Refractive Index
1.615
Storage Temperature
15-25℃
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