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35597-43-4

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Total synthesis and enzyme-substrate interaction of D-, DL-, and L-Phosphinotricine, 'bialaphos' (SF-1293) and its cyclic analogues
DL-Phosphonotricine (3) and its cyclic analogue (4) have been synthesized using the four-component isocyanide condensation of Ugi and Ugi-analogous three-component condensation, respectively. High selectivity of the enzyme-substrate interaction was established with the enzymes α-chymotrypsin, phosphodiesterase I, and alkaline mesintericopeptidase, as well as by separation of the racemic mixture to optical antipodes by the α-chymotripsin. The tripeptide 'bialaphos' (11) and its D-antipode (11a) have been synthesized by the method of activated esters, and the cyclic analogue (15) by the DCC method. It was found that the phospholane L-(5) and the tripeptide (18) exhibit anti-tumour activity.
Natchev, Ivan A.
p. 125 - 131
(2007/10/02)

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74280-72-1
(S)-2-[2-Amino-4-(hydroxy-methyl-phosphinoyl)-butyrylamino]-propionic acid

Chemical Properties

Melting Point: 159-161 C
Boiling Point: 793.2 °C at 760 mmHg
Flash Point:433.5 °C
Density: 1.33 g/cm³
Storage Temp.:Store dry at -4
Vapor Pressure: 1.32E-27mmHg at 25°C
Refractive Index: 1.517
PKA: 2.86±0.50(Predicted)
PSA: 182.29000
LogP: -0.21060

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