4929, TRANSACTIONS OF SECTION B. 
organic compound is producible by vital chemistry or not, we are running the risk 
of blockading whole regions of undiscovered modes of chemical action by falling 
into the belief that known laboratory methods are the equivalents of unknown 
vital methods.’ °° 
I turn now to a no less interesting question than that involved in enzyme 
reactions, namely, the wide distribution in plants and animals of single 
asymmetric substances which if synthesised in the laboratory would be pro- 
duced as inactive mixtures of both asymmetric forms. It has been argued 
that the occurrence of racemic compounds in nature, although infrequent, is a 
proof that in the organism, as in vitro, they are in all cases the initial products 
from which, when separated into antipodes, one of the asymmetric compounds 
is utilised in the life processes and the other left. But whether this be the 
case, or whether only the one asymmetric form result from the synthesis, 
Pasteur firmly held the view that the production of single asymmetric com- 
pounds or their isolation from the inactive mixture of the two forms is the 
prerogative of life. Three methods were devised by Pasteur to effect this isola- 
tion, and in only one of them are living organisms—yeasts or moulds—employed ; 
but Professor Japp, in his address to this Section at Bristol in 1898, emphasised 
the fact, hitherto overlooked, that in the two others, nevertheless, ‘a guiding 
power [is exercised by the operator] which is akin in its results to that of the 
living organism, and is entirely beyond the reach of the symmetric forces of 
inorganic nature.’ Hence, to quote again from his address, ‘only the living 
organism with its asymmetric tissues, or the asymmetric products of the living 
organism, or the living intelligence with its conception of asymmetry, can [bring 
about the isolation of the single asymmetric compound]. Only asymmetry can 
beget asymmetry.’ After an exhaustive review of the subject, Japp came 
to the conclusion that the failure to synthesise single asymmetric compounds 
without the intervention, either direct or indirect, of life is due to a permanent 
disability, and although—as was to be expected—this conclusion was challenged,** 
the only ‘asymmetric syntheses’ effected since that time have been operations 
controlled by the chemical association of an optically active substance with the 
compound undergoing the synthetical change.** 
Recently the problem has assumed a more hopeful character. Ostromiss- 
lensky *° in 1908 made the remarkable discovery that inactive asparagine, 
which is not racemic but a mixture of the dewtro- and Jwvo-forms in molecular 
proportion, gave a separation of one or other isomeride when its saturated 
solution was inoculated by a crystal of glycine—a substance devoid of asym- 
metry. Now Erlenmeyer claims to have achieved a true asymmetric synthesis 
by boiling an aqueous solution of inactive asparagine for sixteen hours, when by 
crystallisation part of the deatro-form separated in an almost pure state.°*. The 
theoretical conclusions which led to this investigation are of much interest 
because they raise afresh the question whether without displacement of the 
individual radicals, and apart from antipodes, more than one compound can exist, 
in the molecule of which two carbon atoms are united by a single linking.** As 
an illustration, reference may be made to the malic-acid series, in which three 
optically active compounds are known, the dextro-acid, the Jcvo-acid, and 
Aberson’s acid.®* In the Jevo-series the three isomerides obtainable by rotation 
°° R. Meldola, Zhe Chemical Synthesis of Vital Products (Arnold, 1904), p. vii. 
“ F. R. Japp, Stereochemistry and Vitalism. Presidential Address to 
Section B (Bristol), British Association Report, 1898, p. 826; cf. K. Pearson, 
Nature, 1898, 58, 495; G. Errara; F. R. Japp, ibid. 616; Ulpiani and Condelli, 
Gazz. chim. ital. 1900, 80[i], 344: Byk, Ber, 1904, 87, 4696; Henle and Haakh, 
Ber. 1908, 41, 4261; Byk, Ber. 1909, 42, 141. 
2 Of. inter alia, McKenzie, Trans. Chem. Soc., 1905, 8%, 1373. 
63 T, von Ostromisslensky, Ber., 1908, 41, 3039. 
64 B®. Erlenmeyer, Biochem. Zeitsch. 1913, 52, 439. 
°° Of. J. Wislicenus, Ueber die rdéumliche Anordnung der Atome in organ- 
ischen Molekulen (Hirkel, Leipzig, 1889), 28; K. Auwers and V. Meyer, Ber., 
1888, 21, 791. 
6° J. H. Aberson, Ber., 1898, 831, 1432; P. Walden, Ber., 1899, 82, 2720. 
