8.52070

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

Novabiochem^®

• Synonym(s): Fmoc-Thr(PO(OBzl)OH)-OH, N-α-Fmoc-O-benzyl-L-phosphothreonine
• Empirical Formula (Hill Notation): C₂₆H₂₆NO₈P
• CAS Number: 175291-56-2
• Molecular Weight: 511.46
• UNSPSC Code: 12352209
• NACRES: NA.22
• MDL number: MFCD00797870

Properties

• Quality Segment: 200
• product line: Novabiochem^®
• assay: ≥90.0% (acidimetric), ≥98% (TLC), ≥98.0% (HPLC)
• form: powder
• reaction suitability: reaction type: Fmoc solid-phase peptide synthesis
• manufacturer/tradename: Novabiochem^®
• application(s): peptide synthesis
• functional group: Fmoc
• storage temp.: −20°C
• SMILES string: [P](=O)(O[C@H]([C@@H](NC(=O)OCC2c3c(cccc3)c4c2cccc4)C(=O)O)C)(OCc1ccccc1)O
• 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

Description

General description

An excellent building block for the preparation of phosphothreonine-containing peptides ^[1,2] by Fmoc SPPS. This derivative can be introduced using standard activation methods, such as PyBOP^® and TBTU. The monoprotected phosphothreonine 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 ^[1].A paper describes the use of this derivative in the preparation of phospholamban ^[3], a 52 residue peptide containing both phosphoserine and phosphothreonine.

Associated Protocols and Technical Articles
Cleavage and Deprotection Protocols for Fmoc SPPS

Literature references

^[1] P. White & J. Beythien in ′Innovations & Perspectives in Solid Phase Synthesis and Combinatorial Libraries, 4th International Symposium′, Mayflower Scientific Ltd., Birmingham, 1996, pp. 557.
^[2] T. Vorherr, et al. (1995) Bioorg. Med. Chem. Lett., 5, 2661.
^[3] H. Schmid, et al., Poster 423 presented at the 15th American Peptide Symposium, Nashville, 1997.

Application

• Development of highly selective 1, 2, 3-triazole-containing peptidic Polo-like kinase 1 Polo-box domain-binding inhibitors: This study explores the synthesis of inhibitors using Fmoc-Thr(PO(OBzl)OH)-OH among other amino acids, showcasing its utility in developing targeted cancer therapies (Zhao et al., 2019).

Analysis Note

Color (visual): white to slight yellow to beige
Appearance of substance (visual): powder
Identity (IR): passes test
Optical rotation α 25/D (c=1 in DMF): -6.5 - -3.5 °
Purity (TLC(CMA1)): ≥ 98 %
Assay (HPLC, area%): ≥ 98.0 % (a/a)
Solubility (1 mmole in 2 ml DMF): clearly soluble
Assay (acidimetric): ≥ 90.0 %
Water (K. F.): ≤ 2.0 %
Ethyl acetate (HS-GC): ≤ 0.5 %
Acetate (IC): ≤ 0.1 %

To see the solvent systems used for TLC of Novabiochem^® products please click here.

Other Notes

Replaces: 04-12-1155

Legal Information

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

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

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: No data available
• flash_point_c: No data available