SYNTHESIS OF D-5-OXAPROLINE AND L-5-OXAPROLINE AND OF A NEW CAPTOPRIL ANALOG
SYNTHESIS OF D-5-OXAPROLINE AND L-5-OXAPROLINE AND OF A NEW CAPTOPRIL ANALOG
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DOI：
10.1002/hlca.19830660424
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发表时间：
1983-01-01
影响因子：
1.8
通讯作者：
HUGUENIN, R
中科院分区：
文献类型：
--
作者：
VASELLA, A;VOEFFRAY, R;HUGUENIN, R
由部分保护的D-甘露糖肟3和乙醛酸酯4原位形成的C-叔丁氧羰基-N-甘露糖基-硝酮5与乙烯的1，3-偶极环加成优先产生（3S）-N-糖基-异恶唑烷6，其转化为3-异恶唑烷-羧酸酯（L-5-氧杂脯氨酸酯）12及其一些衍生物。通过与L-天冬酰胺衍生物的化学相关性证明了12的（S）-构型。D-5-氧杂脯氨酸酯得自相应的N-核糖基-硝酮24。合成了两种保护的二肽，分别含有C-末端-（28）或N-末端-5-氧代脯氨酸（= Opro）（30）。从12开始，制备captopril®类似物1（2），并检测其作为血管紧张素转换酶（ACE）抑制剂的活性。
The 1,3‐dipolar cycloaddition of theC‐t‐butyloxycarbonyl‐N‐mannosyl‐nitrone5, formedin situfrom the partially protectedD‐mannose‐oxime3and the glyoxylate4, to ethylene gave preferentially the (3S)‐N‐glycosyl‐isoxazolidine6which was transformed into the 3‐isoxazolidine‐carboxylate (L‐5‐oxaproline ester)12and into some derivatives thereof. The (S)‐configuration of12was proved by chemical correlation with a derivative ofL‐asparagine. TheD‐5‐oxaproline ester was obtained from the correspondingN‐ribosyl‐nitrone24. Two protected dipeptides containing eitherC‐terminal‐ (28) orN‐terminal‐5‐oxaproline (= Opro) (30) were synthesized. Starting from12, the analogue1of captopril® (2) was prepared and its activity as an inhibitor of the angiotensin‐converting‐enzyme (ACE) was examined.