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Zurückführung der Konfiguration des (natürlichen) Sphingosins auf die der D ‐ erythro ‐2‐Amino‐3,4‐dioxy‐buttersäure. 12. Mitteilung über Sphingosin und Sphingolipoide
Author(s) -
Kiss J.,
Fodor G.,
Bánfi D.
Publication year - 1954
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19540370515
Subject(s) - chemistry , sphingosine , diastereomer , stereochemistry , ozonolysis , amino acid , butyric acid , biochemistry , organic chemistry , receptor
Sphingosine was cleaved by ozonolysis into 2‐hydroxy‐3‐aminobutyrolactone‐hydrochloride, this, in turn, hydrogenated in two steps to a slightly levorotatory 2‐amino‐1, 3,4‐butantriol. The latter proved to be the antipode of the amino‐butantriol obtained on hydrogenation of the γ‐lactone of L ‐ erythro ‐2‐amino‐3, 4‐dihydroxy‐butyric acid. Since the configurations of the four stereoisomeric 2‐amino‐3,4‐dihydroxy butyric acids have already been established, sphingosine belongs to the D ‐ erythro ‐series. On the other hand, the trans ‐ethylenic structure of sphingosine having been elucidated recently, the structure of D ‐ erythro ‐2‐amino‐1,3‐dihydroxy‐4‐ trans ‐octadecene can be assigned to it. These findings and deductions agree well with other pieces of evidence regarding the configuration of dihydro sphingosine, reported previously by Grob and Carter , resp.