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Focus on O-phosphohydroxylysine, O-phosphohydroxyproline, N 1-phosphotryptophan and S-phosphocysteine

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Abstract

The synthesis and chemistry of the lesser-known phosphoamino acids, O-phosphohydroxylysine, O-phosphohydroxyproline, N 1-phosphotryptophan and S-phosphocysteine are described in detail. In addition, where anything at all is known, the biological synthesis, occurrence and functions of these phosphoamino acids are described. Of these phosphoamino acids, only N 1-phosphotryptophan has not been reported to occur in proteins; however, apart from the roles of S-phosphocysteine in the sugar transporter component (EII) and in catalysis by protein phosphotyrosine phosphatase, little is currently known about the biological roles of the phosphoamino acids when they occur as post-translational modifications.

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Notes

  1. Note, the use of D/L by Hubálek et al. (2002) to describe the mixture of configurations at C5 of the lysine residue is incorrect. Either allo/threo or, better, R/S should be used (allo = S, threo = R).

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  1. School of Molecular Sciences (M310), The University of Western Australia, 35 Stirling Highway, Crawley, WA, 6009, Australia

    Matthew J. Piggott & Paul V. Attwood

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  1. Matthew J. Piggott
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  2. Paul V. Attwood
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Correspondence to Paul V. Attwood.

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Piggott, M.J., Attwood, P.V. Focus on O-phosphohydroxylysine, O-phosphohydroxyproline, N 1-phosphotryptophan and S-phosphocysteine. Amino Acids 49, 1309–1323 (2017). https://doi.org/10.1007/s00726-017-2446-x

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