Über die biologische Bedeutung und Synthese von Sulfonsäure-Analoga der Pimelinsäure

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Abstract
Mueller (Proc. Soc. Exp. Biol. and Med. 36: 706. 1937) reported that the growth of certain strains of bacteria was promoted by pimelic acid. However, it has not been shown that pimelic acid is essential for the growth of all bacteria. To det. whether the sulfonic acid analogues of pimelic acid would act as "antivitamins", a number of the analogues were synthesized as follows: 6 g. of pentamethylene-1,5-diisothiocarbamide chlorhydrate were dissolved in 30 ml. water and the soln. saturated with Cl2 at 10[degree]. The penta-methylene-l,5-disulfochloride formed was recrystallized from ether and melted at 65[degree]-66[degree]. Pentamethylene-l,5-disulf-amide, rn. 131[degree], was formed by treating the above sulfo-chloride with aqueous NH4OH soln. To 10 ml. of a concd. aqueous dimethylamine soln. was added, with cooling, 1 g. of pentamethylene-l,5-disulfochloride, and crystals of penta-methylene-l,5-disulfodirnethylarnide, (C9H22O4S2N2), m. 86[degree], obtained. 9 g. of [image]-bromo-n-caproic acid were refluxed for 2 hrs. with a soln. of 8 g. potassium hydrosulfide in 80 ml. of water. The soln. was acidified with H2SO4, the oily precipitate formed dissolved in ether, which was then evaporated and the liquid f-mercapto-n-caproic acid (b.p., 155[degree]-157[degree] at 13 mm. pressure) obtained. When 1.4 g. of this compound were suspended in 6 ml. water and the mixture saturated with Cl2 at 15[degree], n-caproic acid--disulfide (C12H24-O4S2), m. 83[degree], was obtained. Other compounds synthesized were n-caproic acid-e-isothiocarbamide hydrochloride (C7H15-O2N2SCl, m. 106[degree]), n-caproic acid-e-sulfochloride (C6H11O4-SCl, m. 58[degree]-59[degree]), the disodium salt of e-sulfo-n-caproic acid (C6H10O5SNa2), n-caproic acid-e-sulfamide (C6H13O4NS, m. 105[degree]) and n-caproic acid-6-sulfodimethylamide (C8H17O4NS, m. 94[degree]). 15 ml. of nutrient soln. prepd. according to Mueller were placed in centrifuge tubes which were inoculated with various strains of bacteria and kept at 34[degree] or 37[degree] for 7 days. The tubes were centrifugalized and the N content of the bacterial growth detd. by the Kjeldahl method. Of 13 strains of diphtheria bacillus tested, only 2 showed increased growth in the presence of pimelic acid (Strain No. 151, 14-27% increase in growth; Strain No. 8560, 10-19% increase in growth). The above synthesized sulfonic acid analogues of pimelic acid and the sulfamides did not affect the growth of the diphtheria bacteria even when present in high conc. (40 mg. %). Neither n-pentane-l,5-disulfonic acid nor e-sulfo-n-caproic acid nor their sulfamides affected the growth of Escherichia coli Staphylococcus aureus or Streptococcus haemolyticus.

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