Configurational assignment of rhizopodin, an actin-binding macrolide from the myxobacterium Myxococcus stipitatus.
نویسندگان
چکیده
The relative and absolute stereochemistry of the 38-membered myxobacterial polyketide rhizopodin, a potent actin-binding macrolide, was determined by J-based configurational analysis in combination with molecular modeling and chemical derivatization.
منابع مشابه
Natural Products Synthesis
Rhizopodin (1, Scheme 1) is an architecturally unique polyketide macrolide that was originally isolated from the myxobacterium Myxococcus stipitatus by the groups of Hçfle and Reichenbach. It shows potent antifungal and antiproliferative cytotoxicity against a range of tumor cell lines with IC50 values in the low nanomolar range. [1] On a molecular level, 1 disrupts the cytoskeleton of actin by...
متن کاملDesign, synthesis, and biological evaluation of simplified side chain hybrids of the potent actin binding polyketides rhizopodin and bistramide.
The natural products rhizopodin and bistramide belong to an elite class of highly potent actin binding agents. They show powerful antiproliferative activities against a range of tumor cell lines, with IC50 values in the low-nanomolar range. At the molecular level they disrupt the actin cytoskeleton by binding specifically to a few critical sites of G-actin, resulting in actin filament stabiliza...
متن کاملAn Effective Bifunctional Aldehyde Linchpin for Type II Anion Relay Chemistry: Development and Application to the Synthesis of a C16–C29 Fragment of Rhizopodin
The design, synthesis, and validation of a new bifunctional aldehyde linchpin for Type II anion relay chemistry have been achieved. For this linchpin, the initial nucleophilic addition proceeds under Felkin-Anh control to generate the syn-alkoxide, which undergoes a 1,4-Brook rearrangement to relay the negative charge, thus leading to the formation of a dithiane-stabilized carbanion. Subsequent...
متن کاملDiscovery of the rhizopodin biosynthetic gene cluster in Stigmatella aurantiaca Sg a15 by genome mining.
The field of bacterial natural product research is currently undergoing a paradigm change concerning the discovery of natural products. Previously most efforts were based on isolation of the most abundant compound in an extract, or on tracking bioactivity. However, traditional activity-guided approaches are limited by the available test panels and frequently lead to the rediscovery of already k...
متن کاملSaframycin Mx1, a new natural saframycin isolated from a myxobacterium.
A new natural saframycin was discovered in the culture broth of the myxobacterium, Myxococcus xanthus strain Mx x48. The fermentation and isolation of the antibiotic are described. The name, saframycin Mx1, is proposed. The compound appears to interact with cellular DNA.
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید
ثبت ناماگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید
ورودعنوان ژورنال:
- Chemical communications
دوره 41 شماره
صفحات -
تاریخ انتشار 2008