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

• CAS: 175291-56-2
• Catalog Number: ACM175291562-2
• Category: Amino Acids
• Molecular Weight: 511.46
• Molecular Formula: C26H26NO8P
• Description: An excellent building block for the preparation of phosphothreonine-containing peptides by Fmoc SPPS. This derivative can be introduced using standard activation methods, such as PyBOPand 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.A paper describes the use of this derivative in the preparation of phospholamban , a 52 residue peptide containing both phosphoserine and phosphothreonine.
• Synonyms: Fmoc-Thr(PO(OBzl)OH)-OH, N-α-Fmoc-O-benzyl-L-phosphothreonine
• 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); ≥98% (TLC); ≥98.0% (HPLC)
• Form: powder
• Functional Group: Fmoc
• MDL Number: MFCD00797870
• Quality Level: 200
• Reaction Suitability: reaction type: Fmoc solid-phase peptide synthesis
• Storage Temperature: 15-25℃
• Type: Unusual Amino Acids, Analogs of Serine, Threonine, and Statine

Synthetic Use

Upstream Synthesis Route 1

• 73731-37-0
• 100-51-6

• 175291-56-2

Reference: [1] Patent: WO2013/12416, 2013, A1, . Location in patent: Page/Page column 70-71; 75

Upstream Synthesis Route 2

• 175291-55-1

• 175291-56-2

Reference: [1] Bulletin of the Chemical Society of Japan, 1996, vol. 69, # 2, p. 465 - 468

Upstream Synthesis Route 3

• 76101-29-6

• 175291-56-2

Reference: [1] Organic Letters, 2012, vol. 14, # 5, p. 1206 - 1209

Upstream Synthesis Route 4

• 175291-55-1

• 175291-56-2

Reference: [1]Bulletin of the Chemical Society of Japan,1996,vol. 69,p. 465 - 468

Upstream Synthesis Route 5

• 73731-37-0

• 175291-56-2

Reference: [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 4815 - 4823