92264-99-8

Usage

Chemical Properties

Yellow, viscous oil

InChI:InChI=1/C16H24NO8P/c1-16(2,3)24-15(20)17-13(14(18)19)10-11-6-8-12(9-7-11)25-26(21,22-4)23-5/h6-9,13H,10H2,1-5H3,(H,17,20)(H,18,19)/t13-/m0/s1

Upstream product

• 119255-37-7 N^α-(tert-butoxycarbonyl)tyrosine anthraquinon-2-ylmethylester 
• 3978-80-1 Boc-Tyr-OH 
• 92264-95-4 N-(tert-butoxycarbonyl)-L-tyrosyl p-nitrobenzyl ester 
• 127103-00-8 N^α-(tert-butoxycarbonyl)-O-(dimethylphosphono)tyrosine anthraquinon-2-ylmethyl ester 
• 92264-96-5 N-(tert-Butoxycarbonyl)-O-(dimethylphosphono)-L-tyrosyl p-nitrobenzyl ester 

Downstream Products

• 158778-21-3 cyclo 
• 118903-66-5 TFA*H-Tyr(PO₃Me₂)-Val-OMaq 

Relevant academic research and scientific papers

Synthesis of a Phosphotyrosine-Containing Peptide Fragment of the Regulatory Domain of pp60c-src

t-Boc-Tyr(PO3Me2)-OH (4) was utilized in the synthesis of PheThrSerThrGluProGlnTyr(PO3H2)GlnProGlyGluAsnLeu (1), a phosphotyrosine-containing peptide fragment of the regulatory domain of pp60c-src.The protected amino acid 4 was employed during

Synthesis of O-phosphotyrosine-containing peptides: 3. Synthesis of H-Pro-Try(P)-Val-OH via dimethyl phosphate protection and the use of improved deprotection procedures

The phosphorylated derivative N(α)-(tert-butoxycarbonyl)-O-(dimethylphosphono)tyrosine anthraquinon-2-ylmethyl ester, Boc-Tyr(PO3Me2)-OMaq (2), was prepared in high yields by either phosphotriester or ''phosphite-triester'' phosphorylation of Boc-Tyr-OMaq (1). In the former case, either sodium hydride or lithium diisopropylamide was used to generate the phenoxide ion which was then treated with dimethyl phosphorochloridate (MeO)2P(O)Cl. Alternatively, dimethyl N,N-diethylphosphoramidite (MeO)2PNEt2 (15) and 1H-tetrazole were used in the phosphite-triester approach, to effect the quantitative, acid-catalyzed phosphitylation followed by m-chloroperoxybenzoic acid oxidation of the phosphite-triester intermediate. Removal of the 2-methylanthraquinone group (Maq) by reduction with sodium dithionite afforded Boc-Tyr(PO3Me2)-OH (3) in 70-75% overall yield. This derivative was used in the solution-phase synthesis of the tripeptide Boc-Pro-Tyr(PO3Me2)-Val-OMaq (9) by the Boc mode of peptide synthesis, which was followed by the removal of the Maq and Boc groups by successive dithionite reduction and 40% CF3CO2H/CH2Cl2 treatments respectively. Six procedures for the cleavage of the methyl phosphate group by acidolysis or silylolysis from H-Pro-Tyr(PO3Me2)-Val-OH·TFA (11) were examined with the source of hard acid being CF3SO3H, (CH3)3SiBr, (CH3)3SiBr, or CF3SO3Si(CH3)3 and either thioanisole or dimethyl sulfide as the soft nucleophile. While deprotection treatments gave H-Pro-Tyr(P)-Val-OH in modest isolated yields, monitoring with 31P NMR and 13C NMR indicated quantitative deprotection. Enhanced rates of methyl cleavage from the protecting phosphate group were observed with the use of thioanisole.

An Improved One-pot Synthesis of Nα-(tert-Butoxycarbonyl)-O-(O',O"-dialkylphosphoro)-L-tyrosines Using Dialkyl N,N-Diethylphosphoramidites

Nα-(tert-Butoxycarbonyl)-O-(O',O"-dialkylphosphoro)-L-tyrosines 6a-c were prepared in high yields by an efficient one-pot procedure, which involved initial tert-butyldimethylsilyl protection of the carboxy terminus of N-Boc tyrosine 1 followed

SYNTHESIS OF PROTECTED DERIVATIVES OF O-PHOSPHOTYROSINE INCORPORATION IN A HEPTAPEPTIDE

The solid phase synthesis of the phosphopeptide Leu-Arg-Ala-Tyr(P)-Leu-Gly is reported via stepwise incorporation of the protected phosphoamino acid Nα-tert-butyloxycarbonyl-O-dimethyl-phosphono-L-tyrosine.