Amino Acids

“The discoverers of the amino acids are among the elite of science”. This was statement made in a 1931 review of the history of the discovery of the amino acids, and having read the stories of how each of these compounds came to be known, I cannot help but agree.1,2 Just from a technical perspective, I find their ability to separate individual amino acids from hydrolysed proteins, without the relatively modern luxury of chromatography, astounding. Some were discovered by chance, while others were the products of well thought out hypotheses, and diligent searching. I have summarised the origins of the given names in the graphic above, but the stories behind these names are worth telling, and worth telling properly. Therefore, I’m going to tell them over a series of posts, so that I can give them the time and research they deserve! For now, this post, and the graphic that goes with it, serve as a summary.

A note on ordering

The amino acids are notoriously difficult to put in any sensible order. When I had to rote learn their names, structures and codes at university they were often ordered by hydrophobicity, with alphabetical order being the fall-back option. The reviews I’ve been reading order them by the year they were first isolated, but even then they give two separate lists: one by year first synthesised and the other by year first isolated from hydrolysed proteins. It seemed appropriate for my purposes that I order them by the year they were first named. In a couple of cases even this wasn’t straight forward, either because the exact year isn’t known, or because I had to decide which incarnation of the name to use. As I’d put the work in to pin down these dates and look up the original publications, I decided it was worth putting it out there for everyone else, so please enjoy the fully referenced table below! Of particular note are the amino acids that were named before they were discovered, but more on that later…

Amino Acids Table

aEither by synthesis or by hydrolysis of proteins; bThe first known reference to the name of Asparagine is from 1826, but it was implied that this name was already in common use by this point; cCystine is the dimer of cysteine, the dimer was named cystic oxide when it was first isolated in 1810.

 

References

  1. Vickery HB, Schmidt CLA. The History of the Discovery of the Amino Acids. Chem Rev. 1931;9(2):169-318. doi:10.1021/cr60033a001
  2. Bradford Vickery H. The History of the Discovery of the Amino Acids II. A Review of Amino Acids Described Since 1931 as Components of Native Proteins. Adv Protein Chem. 1972;26:81-171. doi:10.1016/S0065-3233(08)60140-0
  3. Braconnot H. Sur la conversion des matieres animales en nouvelles substances par le moyen de l’acide sulfurique. Ann Chim Phys. 1820;13:113-125.
  4. Proust. Sur le Principe qui assaisonne les Fromages. Ann Chim Phys. 1819;10:29-49.
  5. Dulong. Analyse chimique de la racine d’asperge. J Pharm. 1826;12:278-284.
  6. Vauquelin, Robiquet. Découverte d’un nouveau principe végétal dans les Asperges (asparagus sativus. LINN.). Ann Chim. 1806;57:88-93.
  7. Plisson A. Sur l’Identite du Malate acide d’altheine avec l’Asparagine. Ann Chim Phys. 1827;36:175-184.
  8. Berzelius J. Jahresbericht über die Fortschritte der physischen Wissenschaften (Annual Report on the Progress of the Physical Sciences); p338. 1832:338.
  9. Baumann E. Ueber Cystin und Cystein. Zeitschrift für Physiol Chemie. 1884;8(4):299-305. doi:10.1515/bchm1.1884.8.4.299
  10. Wollaston WH. On Cystic Oxide, a New Species of Urinary Calculus. Philos Trans R Soc London. 1810;100:223-230. https://www.jstor.org/stable/107222.
  11. Liebig J. Ueber die Bestandtheile der Flüssigkeiten des Fleisches. Justus Liebigs Ann Chem. 1847;62(3):257-369. doi:10.1002/jlac.18470620302
  12. Liebig J. Baldriansäure und ein neuer Körper aus Käsestoff. Justus Liebigs Ann Chem. 1846;57(1):127-129. doi:10.1002/jlac.18460570112
  13. Berzelius J. Jahresbericht Über Die Fortschritte Der Chemie Und Mineralogie (Annual Report on the Progress of Chemistry and Minerology); P654.; 1848.
  14. Strecker A. Ueber die künstliche Bildung der Milchsäure und einen neuen dem Glycocoll homologen Körper. Justus Liebigs Ann Chem. 1850;75:27-45. doi:10.1002/jlac.18500750103
  15. Cramer E. Ueber die Bestandtheile der Seide. J für Prakt Chemie. 1865;96:76-98. doi:10.1002/prac.18650960111
  16. Werther G. Ueber Glutaminsäure. J für Prakt Chemie. 1866;99(1):6-7.
  17. Hlasiwetz H, Habermann J. Ueber die Proteinstoffe. J für Prakt Chemie. 1873;7(1):397-412. doi:10.1002/prac.18730070147
  18. Schulze E, Bosshard E. Ueber das Glutamin. Berichte der Dtsch Chem Gesellschaft. 1883;16(1):312-315. doi:10.1002/cber.18830160173
  19. Erlenmeyer E, Lipp A. Ueber Phenyl-α-amido-propionsäure. Berichte der Dtsch Chem Gesellschaft. 1882;15:1006-1007.
  20. Schulze E, Barbieri J. Correspondenzen. Berichte der Dtsch Chem Gesellschaft. 1879;12(2):1924-1925. doi:10.1002/cber.187901202184
  21. Schulze E, Steiger E. Ueber einen neuen stickstoffhaltigen Bestandtheil der Keimlinge von Lupinus luteus. Berichte der Dtsch Chem Gesellschaft. 1886;19(1):1177-1180. doi:10.1002/cber.188601901266
  22. Neumeister R. Ueber die Reactionen der Albumosen und Peptone. Z Biol. 1890;26:324-347.
  23. Hopkins FG, Cole SW. A Contribution to the Chemistry of Proteids: Part I. A Preliminary Study of a Hitherto Undescribed Product of Tryptic Digestion. J Physiol. 1901;27(4-5):418-428. doi:10.1113/jphysiol.1901.sp000880
  24. Drechsel E. Ueber die Blidung von Harnstoff aus Eiweiss. Berichte der Dtsch chernischen Gesellschaft. 1890;23:3096-3102.
  25. Drechsel E. Zur Kenntniss der Spaltungsprodukte des Caseïns. J für Prakt Chemie. 1889;39(1):425-429. doi:10.1002/prac.18890390135
  26. Kossel A. Über die basischen Stoffe des Zellkerns. Sitzungsberichte der Königlich Preuss Akad der Wissenschaften zu Berlin. 1896:403-408. https://biodiversitylibrary.org/page/29351956.
  27. a) Ehrlich. Über Isoleucin. Chemiker-Zeitung, Repertorium. 1903;14:201. b) Ehrlich F. Ueber das natürliche Isomere des Leucins. Berichte der Dtsch Chem Gesellschaft. 1904;37(2):1809-1840. doi:10.1002/cber.19040370295
  28. Fischer E, Suzuki U. Synthese von Polypeptiden. III. Derivate der α-Pyrrolidincarbonsaure. Berichte der Dtsch chernischen Gesellschaft. 1904;37:2842-2848.
  29. Willstätter R. Synthese der Hygrinsäure. Berichte der Dtsch Chem Gesellschaft. 1900;33(1):1160-1166. doi:10.1002/cber.190003301201
  30. Fischer E. Spaltung der α-Aminoisovaleriansáure in die optisch activen Componenten. Berichte der Dtsch Chem Gesellschaft. 1906;39:2320-2328.
  31. von Gorup-Besanez E. Ueber die chemischen Bestandtheile einiger Drüsensäfte. Ann der Chemie und Pharm. 1856;98(1):1-43. doi:10.1002/jlac.18560980102
  32. Barger BYG, Coyne FP. The Amino-Acid Methionine; Constitution and Synthesis. Biochem J. 1928;22:1417-1425.
  33. Mueller JH. A new sulphur-containing amino acid isolated from casein. Proc Soc Exp Biol Med. 1922;19(4):161-163.
  34. Meyer CE, Rose WC. The Spatial Configuration of α-amino-β-hydroxy-n-butyric acid. J Biol Chem. 1936;115(3):721-729.
  35. McCoy RH, Meyer CE, Rose WC. Feeding Experiments with Mixtures of Highly Purified Amino Acids. J Biol Chem. 1935;112:283-302.

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