一些与亮氨酸合成和结构测定相关的非异头碳-碳连接的碳水化合物氨基酸。
Some non-anomerically C-C-linked carbohydrate amino acids related to leucine-synthesis and structure determination.
作者信息
Steiner Bohumil, Micová Júlia, Koós Miroslav, Langer Vratislav, Gyepesová Dalma
机构信息
Institute of Chemistry, Slovak Academy of Sciences, Dúbravská cesta 9, SK-84538, Bratislava, Slovakia.
出版信息
Carbohydr Res. 2003 Jun 23;338(13):1349-57. doi: 10.1016/s0008-6215(03)00176-9.
(5'R)-5'-Isobutyl-5'-[methyl (4R)-2,3-O-isopropylidene-beta-L-erythrofuranosid-4-C-yl]-imidazolidin-2',4'-dione was synthesised starting from methyl 2,3-O-isopropylidene-alpha-D-lyxo-pentodialdo-1,4-furanoside via methyl 6-deoxy-6-isopropyl-2,3-O-isopropylidene-alpha-D-lyxo-hexofuranosid-5-ulose applying the Bucherer-Bergs reaction. Its 5'-R configuration was confirmed by X-ray crystallography. Corresponding alpha-amino acid-methyl (5R)-5-amino-5-C-carboxy-5,6-dideoxy-6-isopropyl-alpha-D-lyxo-hexofuranoside (alternative name: 2-[methyl (4R)-beta-L-erythrofuranosid-4-C-yl]-D-leucine) was obtained from the above hydantoin by acid hydrolysis of the isopropylidene group followed by basic hydrolysis of the hydantoin ring. Analogous derivatives with 5S configuration, formed in a minority, were also isolated and characterised.
（5'R）-5'-异丁基-5'-[甲基（4R）-2,3-O-异亚丙基-β-L-赤藓呋喃糖基-4-C-基]-咪唑烷-2',4'-二酮以2,3-O-异亚丙基-α-D-吡喃戊醛糖-1,4-呋喃糖苷为原料，通过6-脱氧-6-异丙基-2,3-O-异亚丙基-α-D-吡喃己糖-5-酮糖，利用布赫尔-贝格斯反应合成。其5'-R构型通过X射线晶体学得到证实。相应的α-氨基酸-甲基（5R）-5-氨基-5-C-羧基-5,6-二脱氧-6-异丙基-α-D-吡喃己糖苷（别名：2-[甲基（4R）-β-L-赤藓呋喃糖基-4-C-基]-D-亮氨酸）由上述乙内酰脲通过异亚丙基的酸水解，随后乙内酰脲环的碱水解得到。还分离并表征了少量形成的具有5S构型的类似衍生物。
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