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Methylphosphinyl (Dmp): A new protecting group of tyrosine suitable for peptide synthesis by use of boc-amino acids

✍ Scribed by Masaaki Ueki; Yoshiyuki Sano; Ichiro Sori; Kozo Shinozaki; Hidekazu Oyamada; Shigeru Ikeda


Publisher
Elsevier Science
Year
1986
Tongue
French
Weight
221 KB
Volume
27
Category
Article
ISSN
0040-4039

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✦ Synopsis


Use of dimethylphosphinyl (Dmp) group as a side-chain phenolic OH protecting group of tyrosine in peptide synthesis was studied. The Dmp group is resistant to trifluoroacetic acid and hydrogenolysis and removed by fluoride ion or liquid HF. The formation of 3-benzyltyrosine from e-benzyl tyrosine in the total deprotection step by HF of protected peptides containing tyrosine is one of the most hazardous side reactions in peptide synthesis.' Recently "low HF" cleavage procedure was reported to be useful to suppress


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