- The total syntheses of D-erythro-sphingosine, N-palmitoylsphingosine (ceramide), and glucosylceramide (cerebroside) via an azidosphingosine analog
-
The total synthesis of D-erythro-sphingosine (9) was performed by a chirospecific method starting from D-galactose via an azidosphingosine intermediate to give highly homogeneous ( > 99.9% C18:1) sphingosine base (9) which contained no observable olefin isomerization by product and was demonstrated to be optically pure by a novel method utilizing Mosher's acid. Ceramide (10) was prepared from this sphingosine (9) with highly homogeneous (99.8% C16:0) palmitic acid by two methods. The cerebroside glucosylceramide (23) was the next sphingolipid in this series to be synthesized in a highly homogeneous form. These three sphingolipids are currently being used for biophysical studies of the structures of their hydrated bio-molecular assemblies.
- Duclos Jr., Richard I
-
p. 111 - 138
(2007/10/03)
-
- SYNTHESES OF D-ERYTHRO-1-DEOXYDIHYDROCERAMIDE-1-SULFONIC ACID AND PHOSPHONOSPHINGOGLYCOLIPID FOUND IN MARINE ORGANISM VIA A COMMON PRECURSOR
-
D-Erythro-1-deoxydihydroceramide-1-sulfonic acid, isolated from alkali-stable hydrogenated lipids in a non-photosynthetic marine diatom, Nitzschia alba, and (2S,3R)-N-palmitoyl-1-O--β-D-galactopyranosyl>-D-sphingosine, found in marine snail Turbo cornutus were synthesized via a common precursor (10) starting from galactose.
- Ohashi, Kinji,Kosai, Shunji,Arizuka, Mitsuo,Watanabe, Takashi,Yamagiwa, Yoshiro,et al.
-
p. 2557 - 2570
(2007/10/02)
-
- SYNTHESIS OF D-ERYTHRO-1-DEOXYDIHYDROCERAMIDE-1-SULFONIC ACID
-
New D-erythro-1-deoxydihydroceramide-1-sulfonic acid, isolated from alkali-stable lipids in a non-photosynthetic marine diatom Nitzschia alba, was synthesized from galactose as a chiral precursor using the Hanessian-Hullar reaction as the key step in the
- Ohashi, Kinji,Yamagiwa, Yoshiro,Kamikawa, Tadao,Kates, Morris
-
p. 1185 - 1188
(2007/10/02)
-