Stereoselective synthesis of lanthionine derivatives in aqueous solution and their incorporation into the peptidoglycan of Escherichia coli
Stereoselective synthesis of lanthionine derivatives in aqueous solution and their incorporation into the peptidoglycan of Escherichia coli
复制标题
DOI：
10.1016/j.bmc.2014.07.023
复制
发表时间：
2014-09-01
影响因子：
3.5
通讯作者：
Luxen, Andre
中科院分区：
文献类型：
--
作者：
Denoel, Thibaut;Zervosen, Astrid;Luxen, Andre
在水溶液中合成了三个非对映异构体(R，R)，(S，S)和羊毛硫氨酸的Meso，具有很高的非对映选择性(~gt；99%)。通过(R)或(R)-半胱氨酸的亲核攻击，打开了两种不同保护的氨基磺酸酯的(S)和(R)对映体。酸化和控制加热释放了游离的羊毛硫素。使用相同的化学方法，还合成了α-苄基羊毛硫氨酸。该方法避免了重结晶富集的需要，为S-35标记这些化合物开辟了道路。此外，还对大肠杆菌W7的体内生物整合进行了研究。未观察到α-苄基羊毛硫氨酸的掺入。相比之下，在体内，(R，R)-羊硫氨酸可以有效地替代中位二氨基苯甲酸，而在(R，R)-羊硫氨酸的存在下，细菌的生长最初是加速的，随后是细胞裂解。在未来，中-[S-35]羊毛硫氨酸可用于研究肽聚糖的生物合成及其周转与细胞生长和分裂的关系。(C)2014爱思唯尔有限公司。保留所有权利。
The three diastereoisomers (R,R), (S,S) and meso of lanthionine were synthesized in aqueous solution with high diastereoselectivity (>99%). The (S) and (R) enantiomers of two differently protected sulfamidates were opened by nucleophilic attack of (R) or (S)-cysteine. Acidification and controlled heating liberated the free lanthionines. Using the same chemistry, an alpha-benzyl lanthionine was also prepared. The proposed method, which avoids the need of enrichment by recrystallization, opens the way to the labelling of these compounds with S-35. Furthermore, in vivo bioincorporation into Escherichia coli W7 was studied. No incorporation of alpha-benzyl lanthionine was observed. In contrast, meso-lanthionine can effectively replace meso-diaminopimelic acid in vivo, while in the presence of (R,R)-lanthionine the initial increase of bacterial growth was followed by cell lysis. In the future, meso-[S-35]lanthionine could be used to study the biosynthesis of peptidoglycan and its turnover in relation to cell growth and division. (C) 2014 Elsevier Ltd. All rights reserved.