- One-pot synthesis of L-felinine
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Conjugate addition of Boc-L-Cys-OH to 3-methylcrotonaldehyde, in situ reduction with sodium borohydride, and in situ deprotection with hydrochloric acid, directly followed by chromatography gives L-felinine in 73% yield. Similar syntheses may produce acid building blocks for combinatorial libraries.
- Daniels, Dwayne L.,Richert, Clemens
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- Synthesis of felinine, 2-amino-7-hydroxy-5,5-dimethyl-4-thiaheptanoic acid
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Several published synthesis procedures reported to lead to (±)-felinine, 2-amino-7-hydroxy-5,5-dimethyl-4-thiaheptanoic acid, a sulfur-containing urinary amino acid of cats (Felis domesticus), were evaluated for their yield. Most of the procedures were found to produce an amino acid isomeric with felinine and the structural assignment of this isomer has been determined as 2-amino-7-hydroxy-7-methyl-4-thiaoctanoic acid. The yield for the only evaluated synthesis procedure shown to produce felinine was found to be low. A new high-yielding method for the synthesis of (±)-felinine is presented.
- Hendriks, Wouter,Woolhouse, Anthony,Tarttelin, Michael,Moughan, Paul
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- Volatile organic sulfur-containing constituents in Poncirus trifoliata (L) Raf. (Rutaceae)
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During our screening of plant materials to find new natural fragrance and flavor ingredients, we discovered two series of 3-sulfanylalkyl alkanoates in a peel extract of fruits of wild-growing Poncirus trifoliata (L) Raf. (Rutaceae), a species closely related to Citrus. The two series belong to alkanoates of 3-methyl-3-sulfanylbutan-1-ol and 3-sulfanylhexan-1-ol, respectively, and thus are members of a family of natural molecules having in common a 1,3-positioned O,S moiety. The alkanoate residues comprise all even-numbered saturated fatty acids from C2 (acetate) to C18 (octadecanoate). Among the 20 sulfur-containing compounds identified, 14 are described for the first time as naturally occurring in a botanical species. Several cysteine-S-conjugates were synthesized as hypothetical precursors of the new volatile sulfur-containing constituents, where after S-(3-hydroxy-1,1-dimethylpropyl)-L-cysteine, S-[3-(acetyloxy)-1,1- dimethylpropyl]-L-cysteine, and S-[1-(2-hydroxyethyl)butyl]-L-cysteine were identified in the fruit peel. No cysteine-S-conjugates were detected in the fruit juice.
- Starkenmann, Christian,Niclass, Yvan,Escher, Sina
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p. 4511 - 4517
(2008/09/20)
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