1583-65-9Relevant academic research and scientific papers
Potent non-benzoquinone ansamycin heat shock protein 90 inhibitors from genetic engineering of Streptomyces hygroscopicus
Menzella, Hugo G.,Tran, Thomas-Toan,Carney, John R.,Lau-Wee, Janice,Galazzo, Jorge,Reeves, Christopher D.,Carreras, Christopher,Mukadam, Sophie,Eng, Sara,Zhong, Ziyang,Timmermans, Pieter B. M. W. M.,Murli, Sumati,Ashley, Gary W.
supporting information; experimental part, p. 1518 - 1521 (2010/02/28)
Inhibition of the protein chaperone Hsp90 is a promising new approach to cancer therapy. We describe the preparation of potent non-benzoquinone ansamycins. One of these analogues, generated by feeding 3-amino-5-chlorobenzoic acid to a genetically engineer
Conformational flexibility of tetralactam macrocycles and their intermolecular hydrogen-bonding patterns in the solid state
Zhu, Sascha S.,Nieger, Martin,Daniels, Joerg,Felder, Thorsten,Kossev, Iordan,Schmidt, Thomas,Sokolowski, Moritz,Voegtle, Fritz,Schalley, Christoph A.
experimental part, p. 5040 - 5046 (2009/12/26)
Despite their rigid scaffold, tetralactam macrocycles (TLMs) display a remarkable degree of conformational flexibility, as revealed by analysis of the corresponding X-ray crystal structures. This flexibility is not limited to the rotatability of the TLM amide groups but also applies to the m-xylene rings, and it thus has a great impact on the overall shape of the macrocycle cavity. The conformational properties of the TLMs give rise to a broad variety of intermolecular hydrogen-bonding patterns, including infinite ladders, an interesting catemer motif, and short C-H... O=C hydrogen bonds. These results are in accord with previous theoretical calculations, support a structural model proposed earlier for an interpretation of scanning tunneling microscopy images, and substantially contribute to the understanding of the adaptability of macrocyclic scaffolds, which is crucial for guest binding or templated syntheses with TLMs.
Macrolactams by engineered biosynthesis
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Page/Page column 15, (2008/12/07)
Macrolactams are made by feeding aromatic amino acids as replacement starter units to a mutant strain of the geldanamycin-producing microorganism Streptomyces hygroscopicus var. geldanus NRRL 3602, wherein the gene cluster encoding enzymes for the biosynt
Design, synthesis, and incorporation of a β-turn mimetic in angiotensin II forming novel pseudopeptides with affinity for AT1 and AT2 receptors
Rosenstr?m, Ulrika,Sk?ld, Christian,Lindeberg, Gunnar,Botros, Milad,Nyberg, Fred,Karlén, Anders,Hallberg, Anders
, p. 6133 - 6137 (2007/10/03)
A benzodiazepine-based β-turn mimetic has been designed, synthesized, and incorporated into angiotensin II. Comparison of the mimetic with β-turns in crystallized proteins showed that it most closely resembles a type II β-turn. The compounds exhibited hig
A lockable light-driven molecular shuttle with a fluorescent signal
Wang, Qiao-Chun,Qu, Da-Hui,Ren, Jun,Chen, Kongchang,Tian, He
, p. 2661 - 2665 (2007/10/03)
A turn on! A lockable photodriven molecular shuttle is based on a [2]rotaxane that consists of an α-cyclodextrin threaded by a stilbene derivative. The fluorescent signals originate from the naphthalimide stopper and indicate the position of the shuttle. Once unlocked, the device can be turned on by irradiation at 335 nm and turned off by irradiation at 280 nm. The shuttle can be locked or unlocked by the addition acid or alkali, respectively (see picture).
Hydrazide-Based Quadruply Hydrogen-Bonded Heterodimers. Structure, Assembling Selectivity, and Supramolecular Substitution
Zhao, Xin,Wang, Xiao-Zhong,Jiang, Xi-Kui,Chen, Ying-Qi,Li, Zhan-Ting,Chen, Guang-Ju
, p. 15128 - 15139 (2007/10/03)
This paper describes the synthesis, self-assembly, and characterization of a new class of highly stable hydrazide-based quadruply hydrogen-bonded heterodimers. All of the hydrazide-derived heterodimers possess the complementary ADDA-DAAD hydrogen-bonding sequences. Hydrazide derivatives 1, which has two intramolecular S(6) RO...H-N hydrogen bonds, and 2 complex to afford two fastly exchanging isomeric heterodimers 1·2 and 1·2′ in chloroform, as a result of two different conformational arrangements of 2. An average binding constant Kassoc of 4.7 × 104 M-1 was determined for heterodimer 1·2 and 1·2′ by 1H NMR titration of 1 with changing 2 in chloroform-d. In contrast, 1 binds 11 and 12, both of which are introduced with two intramolecular S(6) hydrogen bonds, to exclusively afford heterodimers 1·11 and 1·12, with Kassoc values of 1.8 × 104 and 5.0 × 102 M-1, respectively. Fluorine-containing 19, which has a hydrazide skeleton identical to that of 1 but two intramolecular S(6) F...H-N hydrogen bonds, can also complex with 2, 11, and 12, to afford heterodimers 19·2, 19·2′, 19·11, and 19·12, with Kassoc values of of 1.2 × 104 (average value for 19·2 and 19·2′), 5.4 × 103, and 1.9 × 102 M-1, respectively. The structures of the new heterodimers have been proven with NOESY, IR, and VPO (for some of the heterodimers) experiments. Moreover, 1 and 19 can also strongly bind 2,7-dilauroylamido-1,8-naphthyridine 23 to afford dimers 1·23 and 19·23 with Kassoc values of 6.0 × 105 and 1.4 × 105 M-1, respectively. Adding 1 to the 1:1 solution of 23 and 1-octyl-3-(4-oxo-3,4-dihydro-pyrido[2,3-d]pyrimidin-2-yl)urea 24 or 1-octyl-3-(4-oxo-1,4-dihydropyrimidin-2-yl)urea 25, which had been developed initially by Zimmerman and Meijer, respectively, induces dimers 23·24 and 23·25 to dissociate, leading to the formation of dimers 1·23 and 24·24 or 25·25, respectively. The new hydrazide-based hydrogen-bonding modules described are useful building blocks for self-assembly and open a new avenue to recognition between discrete supramolecular species.
