By Noyes W

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Hydrolysis o f the original sample to the corresponding carbamate, G T X 3 (5), w o u l d increase the toxicity o f the sample 6-fold, to 1400 mouse units. Subsequent epimerization o f the hydrolysate, 5, to a 4:1 mixture o f the carbamates GTX2 (3) and 5 (or hydrolysis o f the epimeric sulfamates 4 and 6 to the same mixture o f carbamates) w o u l d then change the toxicity to 1,120 mouse units. T h e observed toxicity and composition o f the hypothetical sample w h i c h started as pure 6 may l i e anywhere w i t h i n the indicated bounds as these interconversions occur.

It can be increased at any point by hydrolysis, toward the toxicity shown o n the upper line. T h e highest toxicity w i l l be attained i f the hydrolysis is performed o n 6 prior to epimerization, resulting i n 5. Hydrolysis o f the epimeric 4 and 6, o r epimerization o f the hydrolysate, will ultimately result i n a stable, equilibrated mixture o f the epimers 3 and 5, with a slightly lower toxicity. T h e hypothetical sample discussed here, containing pure 6 at the start, was chosen because it is the limiting case among the k n o w n toxins.

Ch003 the sample. 05 M H C I added in the final mixture and intended to give approximately p H 3), is quite insufficient to ensure complete sulfamate hydrolysis. However, trace hydrolysis is difficult to avoid and, d u e to the substantially higher potency o f the hydrolysis products, makes it difficult to obtain reliable values for the potency o f samples containing the sulfamates. Figure 10 summarizes these considerations for a hypothetical sample containing 1 / i m o l o f saxitoxin C 2 (6), w h i c h is both a sulfamate and an 11-^-hydroxysulfate.

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