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CAS 158171-15-4

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N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-O-phosphono-L-serine

Description:
N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-O-phosphono-L-serine, commonly referred to as Fmoc-Ser(PO3H2), is a phosphonated derivative of the amino acid serine. This compound features a fluorenylmethoxycarbonyl (Fmoc) protecting group, which is widely used in peptide synthesis to protect the amino group of amino acids. The presence of the phosphono group introduces unique properties, such as increased polarity and potential for enhanced biological activity, making it useful in various biochemical applications. The structure includes a serine backbone, which contributes to its role in protein synthesis and modification. This compound is typically utilized in the synthesis of phosphopeptides and can serve as a substrate for kinases or other enzymes that interact with phosphorylated amino acids. Its stability under standard laboratory conditions and compatibility with various coupling reagents make it a valuable tool in organic and medicinal chemistry. Overall, N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-O-phosphono-L-serine is significant in research involving peptide chemistry and phosphoproteomics.
Formula:C18H18NO8P
InChI:InChI=1S/C18H18NO8P/c20-17(21)16(10-27-28(23,24)25)19-18(22)26-9-15-13-7-3-1-5-11(13)12-6-2-4-8-14(12)15/h1-8,15-16H,9-10H2,(H,19,22)(H,20,21)(H2,23,24,25)/t16-/m0/s1
InChI key:InChIKey=LGDJNCRIHRFKML-INIZCTEOSA-N
SMILES:C(OC(N[C@@H](COP(=O)(O)O)C(O)=O)=O)C1C=2C(C=3C1=CC=CC3)=CC=CC2
Synonyms:
  • N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-O-phosphono-L-serine
  • L-Serine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-, dihydrogen phosphate (ester)
  • Fmoc-pSer-OH
  • L-Serine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-O-phosphono-
  • Fmoc-phospho-L-serine
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