Absolute Configuration and Crystal Structure of a Phosphonate Analogue of Tyrosine Produced by Actinomycetes |
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| Authors: | Wanda Sawka-dobrowolska Janusz Kowalik Tadeusz Glowiak |
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| Affiliation: | 1. Institute of Chemistry, University of Wroclaw , 14 Joliot-Curie, 50-383 , Wroclaw , Poland;2. Institute of Organic and Physical Chemistry, Technical University , 50-370, Wroclaw , Poland |
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| Abstract: | Abstract Levorotatory 1-amino-2-(4-hydroxyphenyl)ethylphosphonic acid (TyrP) of unknown configuration is a part of hypotensive tri-peptides produced by Actinomycetes1 and is the only 1-aminoalkane phosphonate found so far in living organisms. Nitration of enantiomers of PheP followed by reduction of the p-nitro group and diazotization yielded enantiomers of TyrP of specific rotations +67 and ?67° (c.0.9;1n HCl). Single crystal X-ray analysis showed S configuration for dextrorotatory TyrP. Thus, natural levorotatory TyrP has the R configuration and belongs to the L series of aminoacids. |
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