scholarly journals Revision of the structure of isochaetoglobosin Db based on NMR analysis and biosynthetic consideration

RSC Advances ◽  
2020 ◽  
Vol 10 (40) ◽  
pp. 23969-23974
Author(s):  
Yan-duo Wang ◽  
Yuan-yuan Li ◽  
Xiang-mei Tan ◽  
Lin Chen ◽  
Zhong-qi Wei ◽  
...  
Keyword(s):  
Pyrrole Ring ◽  
Nmr Analysis ◽  
Macrocyclic Ring

Isochaetoglobosin Db is a new chaetoglobosin possessing a unique 3,4-substituted pyrrole ring isolated and named by Qiu et al., and it is different from any one of the 14 sub-types in the macrocyclic ring of chaetoglobosins classified in our previous work.

"Click chemistry" in the synthesis of the first glycoconjugates of bacteriochlorin series

2012 ◽  
Vol 16 (10) ◽  
pp. 1094-1109 ◽  
Author(s):  
Mikhail A. Grin ◽  
Ivan S. Lonin ◽  
Leonid M. Likhosherstov ◽  
Olga S. Novikova ◽  
Anna D. Plyutinskaya ◽  
...  
Keyword(s):  
Click Chemistry ◽  
Cell Line ◽  
Triple Bond ◽  
Pyrrole Ring ◽  
2D Nmr ◽  
Bacteriochlorophyll A ◽  
Dipolar Cycloaddition ◽  
Nmr Analysis ◽  
Hep2 Cell ◽  
Imide Ring

A regioselective synthesis of glycoconjugates based on bacteriochlorophyll a and lactose derivatives has been carried out. The conjugation was achieved via 1,3-dipolar cycloaddition of bacteriochlorins containing a terminal triple bond and a lactose azide derivative. The conjugates obtained in this way had one or two disaccharide fragments attached to pyrrol A, the exocyclic imide ring of the tetrapyrrolyc macrocycle, or to both positions. Exhaustive NMR analysis by 1D and 2D NMR experiments ( 1H-1H COSY, TOCSY, ROESY, 1H-13C HSQC, HMBC, and 1H-15N HMBC) allowed us to determine the structures and configurations of the glycoconjugates obtained. A bioassay of the glycoconjugates using the Hep2 cell line showed that the highest efficiency was observed for the glycosylated bacteriopurpurinimide containing a lactose residue at pyrrole ring A.

A Hydrogen Bond Between Linear Tetrapyrrole and Conserved Aspartate Causes the Far-Red Shifted Absorption of Phytochrome Photoreceptors

2020 ◽  
Author(s):  
Egle Maximowitsch ◽  
Tatiana Domratcheva
Keyword(s):  
Hydrogen Bond ◽  
Light Adaptation ◽  
Positive Charge ◽  
Pyrrole Ring ◽  
Md Simulations ◽  
Spectral Shift ◽  
Specific Domain ◽  
Study Guides ◽  
Rational Engineering ◽  
Tuning Mechanism

Photoswitching of phytochrome photoreceptors between red-absorbing (Pr) and far-red absorbing (Pfr) states triggers light adaptation of plants, bacteria and other organisms. Using quantum chemistry, we elucidate the color-tuning mechanism of phytochromes and identify the origin of the Pfr-state red-shifted spectrum. Spectral variations are explained by resonance interactions of the protonated linear tetrapyrrole chromophore. In particular, hydrogen bonding of pyrrole ring D with the strictly conserved aspartate shifts the positive charge towards ring D thereby inducing the red spectral shift. Our MD simulations demonstrate that formation of the ring D–aspartate hydrogen bond depends on interactions between the chromophore binding domain (CBD) and phytochrome specific domain (PHY). Our study guides rational engineering of fluorescent phytochromes with a far-red shifted spectrum.

Highly nonplanar macrocyclic ring conformation in the crystal structures of Ni(II) and Cu(II) octaphenylporphyrins

2018 ◽  
Vol 59 (2) ◽  
Author(s):  
P. Bhyrappa ◽  
◽  
M. Sankar ◽  
K. Karunanithi ◽  
B. Varghese ◽  
...  
Keyword(s):  
Crystal Structures ◽  
Ring Conformation ◽  
Macrocyclic Ring

Synthesis and Structure Assignment of 2-(4-Methoxybenzyl)cyclohexyl β-D-Glucopyranoside Enantiomers

2006 ◽  
Vol 71 (10) ◽  
pp. 1470-1483 ◽  
Author(s):  
David Šaman ◽  
Pavel Kratina ◽  
Jitka Moravcová ◽  
Martina Wimmerová ◽  
Zdeněk Wimmer
Keyword(s):  
Analytical Data ◽  
Chiral Hplc ◽  
Nmr Analysis ◽  
Target Structure ◽  
Enantiomerically Pure ◽  
Whole Cells ◽  
H Nmr ◽  
Structure Assignment ◽  
Related Compounds ◽  
C Nmr

Glucosylation of the cis- and trans-isomers of 2-(4-methoxybenzyl)cyclohexan-1-ol (1a/1b, 2a/2b, 1a or 2a) was performed to prepare the corresponding alkyl β-D-glucopyranosides, mainly to get analytical data of pure enantiomers of the glucosides (3a-6b), required for subsequent investigations of related compounds with biological activity. One of the employed modifications of the Koenigs-Knorr synthesis resulted in achieving 85-95% yields of pure β-anomers 3a/3b, 4a/4b, 3a or 4a of protected intermediates, with several promoters and toluene as solvent, yielding finally the deprotected products 5a/5b, 6a/6b, 5a or 6a as pure β-anomers. To obtain enantiomerically pure β-anomers of the target structure (3a, 4a, 5a and 6a) for unambiguous structure assignment, an enzymic reduction of 2-(4-methoxybenzyl)cyclohexan-1-one by Saccharomyces cerevisiae whole cells was performed to get (1S,2S)- and (1S,2R)-enantiomers (1a and 2a) of 2-(4-methoxybenzyl)cyclohexan-1-ol. The opposite enantiomers of alkyl β-D-glucopyranosides (5b and 6b) were obtained by separation of the diastereoisomeric mixtures 5a/5b and 6a/6b by chiral HPLC. All stereoisomers of the products (3a-6b) were subjected to a detailed 1H NMR and 13C NMR analysis.

scholarly journals Structural Characterization of a Polysaccharide from Gastrodia elata and Its Bioactivity on Gut Microbiota

Molecules ◽  
2021 ◽  
Vol 26 (15) ◽  
pp. 4443
Author(s):  
Jiangyan Huo ◽  
Min Lei ◽  
Feifei Li ◽  
Jinjun Hou ◽  
Zijia Zhang ◽  
...  
Keyword(s):  
Molecular Weight ◽  
Citric Acid ◽  
Gut Microbiota ◽  
Structural Characterization ◽  
Hot Water ◽  
Nmr Analysis ◽  
Gastrodia Elata ◽  
Hot Water Extraction ◽  
Hydroxybenzyl Alcohol

A novel homogeneous polysaccharide named GEP-1 was isolated and purified from Gastrodia elata (G. elata) by hot-water extraction, ethanol precipitation, and membrane separator. GEP-1, which has a molecular weight of 20.1 kDa, contains a polysaccharide framework comprised of only glucose. Methylation and NMR analysis showed that GEP-1 contained 1,3,6-linked-α-Glcp, 1,4-linked-α-Glcp, 1,4-linked-β-Glcp and 1,4,6-linked-α-Glcp. Interestingly, GEP-1 contained citric acid and repeating p-hydroxybenzyl alcohol as one branch. Furthermore, a bioactivity test showed that GEP-1 could significantly promote the growth of Akkermansia muciniphila (A. muciniphila) and Lacticaseibacillus paracasei (L.paracasei) strains. These results implied that GEP-1 might be useful for human by modulating gut microbiota.

scholarly journals Mono- and Dinitro-BN-Naphthalenes: Formation and Characterization

Molecules ◽  
2021 ◽  
Vol 26 (14) ◽  
pp. 4209
Author(s):  
Mao-Xi Zhang ◽  
Nathaniel B. Zuckerman ◽  
Philip F. Pagoria ◽  
Bradley A. Steele ◽  
I-Feng Kuo ◽  
...  
Keyword(s):  
Electron Density ◽  
Nmr Analysis ◽  
X Ray ◽  
Boron Nitrogen

Mono- and dinitro-BN-naphthalenes, i.e., 1-nitro-, 3-nitro-, 1,6-dinitro-, 3,6-dinitro-, and 1,8-dinitro-BNN, were generated in the nitration of 9,10-BN-naphthalene (BNN), a boron–nitrogen (BN) bond-embedded naphthalene, with AcONO2 and NO2BF4 in acetonitrile. The nitrated products were isolated and characterized by NMR, GC-MS, IR, and X-ray single crystallography. The effects of the nitration on the electron density and aromaticity of BNN were evaluated by B-11 NMR analysis and HOMA calculations.

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