158171-13-2

Upstream product

• 100-51-6 benzyl alcohol 
• 108-18-9 diisopropylamine 
• 56183-63-2 bis(diisopropylamino)chlorophosphine 
• 115-20-8 1,1,1-trichloroethanol 
• 108549-21-9 benzyl-N,N,N',N'-tetraisopropylphosphorodiamidite 

Downstream Products

• 158171-17-6 {(S)-2-(Benzyloxy-hydroxy-phosphoryloxy)-1-[(S)-1-(di-p-tolylmethyl-carbamoyl)-ethylcarbamoyl]-ethyl}-carbamic acid 9H-fluoren-9-ylmethyl ester 
• 175291-55-1 (2S,3R)-3-[Benzyloxy-(2,2,2-trichloro-ethoxy)-phosphoryloxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid 2-oxo-2-phenyl-ethyl ester 
• 175291-56-2 Fmoc-L-Thr(HPO₃Bzl)-OH 
• 175291-54-0 Fmoc-Ser-OPac 
• 158171-14-3 (S)-3-(Benzyloxy-hydroxy-phosphoryloxy)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid 

Relevant academic research and scientific papers

Synthetic study of phosphopeptides related to heat shock protein FLSP27

Two kinds of phosphoserine-containing peptides related to HSP27 were synthesized by the Boc- or Fmoc-mode solid-phase method based on prephospholylation strategy. In the case of the Boc strategy, the O-phosphono group of the phosphoserine residue was protected with the cyclopentyl or cyclohexyl group. On the other hand, N(x)-Fmoc-O-[(benzyloxy)-hydroxyphosphinyl]serine was employed in case of the Fmoc strategy. Consequently, it has become feasible to utilize conventional solid-phase methods for synthesizing any phosphopeptides which are required to elucidate biochemical significance of protein phosphorylation.

Preparations of Nα-Fmoc-O-[(benzyloxy)hydroxyphosphinyl] β-hydroxy α-amino acid derivatives

Nα-Fmoc-O-[(benzyloxy)hydroxyphosphinyl]serine and Nα-Fmoc-O-[(benzyloxy)hydroxyphosphinyl]threonine were prepared in order to be utilized for the synthesis of phosphoserine- or phosphothreonine-containing peptides based on the Fmoc-mode pre-phosphorylation strategy. These derivatives were obtained as crystalline compounds, which are favorable for use as building blocks for an automated peptide synthesis by a solid-phase method.

An Efficient Procedure for Solid Phase Synthesis of Phosphopeptides by the Fmoc Strategy

The Fmoc-mode solid-phase method was succesfully applied to establish a practical procedure for the synthesis of phosphopeptides.Both Fmoc-phosphoserine with free phosphoric moiety and its monobenzyl phosphate derivative were examined as one of starting materials for the synthesis of peptides.The employment of the latter gave better result in respects of the yield and purity of the product than that obtained with the former.