Reductase of Mutanobactin Synthetase Triggers Sequential C-C Macrocyclization, C-S Bond Formation, and C-C Bond Cleavage

被引：7

作者：

Wang, Min ^{[1
,2
,3
]}

Xie, Zhoujie ^{[1
]}

Tang, Shoubin ^{[3
]}

Chang, Ee Ling ^{[3
]}

Tang, Yue ^{[1
,2
,3
]}

Guo, Zhengyan ^{[2
]}

Cui, Yinglu ^{[1
]}

Wu, Bian ^{[1
,2
]}

Ye, Tao ^{[3
]}

Chen, Yihua ^{[1
,2
]}

机构：

[1] Chinese Acad Sci, Inst Microbiol, Beijing, Peoples R China

[2] Univ Chinese Acad Sci, Beijing, Peoples R China

[3] Tsinghua Univ, Shenzhen Int Grad Sch, Peking Univ, Shenzhen Grad Sch, Shenzhen, Peoples R China

来源：

ORGANIC LETTERS | 2020年 / 22卷 / 03期

关键词：

BIOSYNTHESIS; POLYKETIDE; CYCLIZATION; INHIBITORS; MECHANISM;

D O I：

10.1021/acs.orglett.9b04501

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Mutanobactins (MUBs) and their congeners that contain a macrocycle and/or a thiazepane ring are lipopeptides from Streptococcus mutans, a major causative agent of dental caries. Here we show that the C-terminal reductase domain of MubD releases the lipohexapeptide intermediates in an aldehyde form, which enables a spontaneous C-C macrocyclization. In the presence of a thiol group, the macrocyclized MUBs can further undergo spontaneous C-S bond formation and C-C bond cleavage to generate diverse MUB congeners.

引用

页码：960 / 964

页数：5

共 50 条

[31] C-C Bond Formation in Diiron Complexes
Mazzoni, Rita
Salmi, Mauro
Zanotti, Valerio
CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (33) : 10174 - 10194
[32] Oxidative C-S bond cleavage reaction of DMSO for C-N and C-C bond formation: new Mannich-type reaction for β-amino ketones
Sun, Kai
Lv, Yunhe
Zhu, Zhonghong
Zhang, Liping
Wu, Hankui
Liu, Lin
Jiang, Yongqing
Xiao, Beibei
Wang, Xin
RSC ADVANCES, 2015, 5 (04): : 3094 - 3097
[33] Immobilization of Aldolase for C-C Bond Formation
Aragon, Caio C.
Palomo, Jose M.
Filice, Marco
Mateo, Cesar
CURRENT ORGANIC CHEMISTRY, 2016, 20 (11) : 1243 - 1251
[34] Fluorine Effects for Tunable C-C and C-S Bond Cleavage in Fluoro-Julia-Kocienski Intermediates
Kang, Lei
Lin, Yongjia
Gao, Zeng
Zhang, Jinlong
Yang, Huameng
Qian, Jinlong
Peng, Qian
Jiang, Gaoxi
CCS CHEMISTRY, 2021, 3 (06): : 1678 - 1689
[35] Benzaldehyde lyase catalyzed cross benzoin condensation reactions with C-C bond breaking and C-C bond formation
Bilir, Gokcil
Demir, Ayhan S.
NEW BIOTECHNOLOGY, 2012, 29 : S86 - S86
[36] C-C BOND FORMATION AND C-H BOND-CLEAVAGE IN REDOX REACTIONS OF RUTHENIUM COMPLEXES
SAUNDERS, DR
MAWBY, RJ
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1984, (03) : 140 - 141
[37] Intramolecular cycloisomerization of a propanes via NHC palladium-catalyzed cascade C-C bond cleavage/C-H activation/C-C bond formation
Yang, Yewei
Huang, Xian
SYNLETT, 2008, (09) : 1366 - 1370
[38] Electrochemical Oxidative C-C Bond Cleavage of Ketones for C-N Bond Formation: A Route to Amides
He, Yonghui
Zeng, Liang
Li, Ming
Gu, Lijun
Zhang, Shengyong
Li, Ganpeng
JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (19): : 12622 - 12631
[39] Transition-Metal-Catalyzed C-C Bond Formation from C-C Activation
Song, Feijie
Wang, Biqin
Shi, Zhang-Jie
ACCOUNTS OF CHEMICAL RESEARCH, 2023, 56 (21) : 2867 - 2886
[40] Iodine-Promoted One-Pot Multicomponent Chemoselective Reaction for C-C/C-N and C-C/C-S Bond Formation Using Thiols
Panigrahi, Ahwan
Muniraj, Nachimuthu
Prabhu, Kandikere Ramaiah
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (35) : 5780 - 5784

← 1 2 3 4 5 →