Formation of diastereoisomeric piperazine-2,5-dione from DL-alanine in the presence of olivine and water.
Formation of diastereoisomeric piperazine-2,5-dione from DL-alanine in the presence of olivine and water.
复制标题
在橄榄石和水存在下，由 DL-丙氨酸形成非对映异构哌嗪-2,5-二酮。
DOI：
10.1007/s11084-016-9500-7
复制
发表时间：
2017
期刊：
影响因子：
--
通讯作者：
H.
中科院分区：
文献类型：
--
作者：
Fuchida;S.;Naraoka;H. and Masuda;H.
将dl-丙氨酸（Ala）与/不与粉末状橄榄石和水在120 °C下加热8天以研究哌嗪-2，5-二酮（二酮哌嗪，DKP）的非对映异构体的形成。当仅dl-Ala与少量水加热时，8天后有3.0%的dl-Ala转化为顺式和反式DKP。当不加水时，加热后未检测到DKP。少量水的存在是在热条件下控制肽生产速率的重要因素。当DL-丙氨酸与橄榄石粉加热8天时，顺式和反式DKP的产率分别为6.8%和4.9%。与反式DKP相比，顺式DKP的高产率归因于顺式DKP更高的热稳定性。在加热8天后，不含橄榄石的顺式-DKP的非对映异构体过量为7.3%，而在橄榄石存在下获得高得多的值16.3%。综上所述，这些结果表明，橄榄石不仅是一种有效的催化剂形成DKP，但它也发挥了重要作用，在确定这些环状二肽的非对映异构体的选择性。
dl-Alanine (Ala) was heated with/without powdered olivine and water at 120 °C for 8 days to investigate the formation of the diastereoisomers of piperazine-2,5-dione (diketopiperazine, DKP). When onlydl-Ala was heated with a small amount of water, 3.0 % ofdl-Ala changed tocis- andtrans-DKP after 8 days. DKPs were not detected after heating when no water was added. The presence of a small amount of water is important factor controlling peptide production rates under thermal conditions. When DL-Ala was heated with olivine powder for 8 days, the yields ofcis- andtrans-DKP were 6.8 and 4.9 %, respectively. The high yield ofcis-DKP compared withtrans-DKP was attributed to greater thermal stability ofcis-DKP. After heating for 8 days, the diastereoisomeric excess ofcis-DKP without olivine was 7.3 %, whereas a much higher value of 16.3 % was obtained in the presence of olivine. Taken together, these results show that olivine is not only an efficient catalyst for the formation of DKPs but that it also play a significant role in determining the diastereoisomer selectivity of these cyclic dipeptides.