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

• CAS: 175291-56-2
• Catalog Number: ACM175291562-1
• Category: Amino Acids
• Molecular Weight: 511.5
• Molecular Formula: C26H26NO8P
• 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
• 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
• Impurity Content: 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

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