Lactic acid, the most important hydroxycarboxylic acid, is now commercially produced by the fermentation of sugars present in biomass. In addition to its use in the synthesis of biodegradable polymers, lactic acid can be regarded as a feedstock for the green chemistry of the future. Different po...

Eight sugar-modified pyrrolopyrimidine nucleoside analogs related to the antibiotic sangivamycin were evaluated in cell culture against herpes simplex types 1 (HSV-1) and 2 (HSV-2), cytomegalovirus (CMV), adenovirus, and visna virus. Five of the compounds were highly active against most of the v...

The pyrrolopyrimidine, sangivamycin, and the adenosine analog, xylosyladenine, were examined for their effects on the synthesis and methylation of polysomal RNA in Ehrlich ascites tumor cells in vitro. The synthesis of non-polyriboadenylic acid (non-poly (A) −) and poly(A)-containing RNA was inh...

The molecular effects of the pyrrolopyrimidine analogs, sangivamycin and thiosangivamycin, on RNA and DNA synthesis were examined in L1210 cells in vitro. Pretreatment of cells for 30 min with either sangivamycin or thiosangivamycin resulted in a median inhibitory dose of 1 × 10−5 M and 2 × 10...

A number of 7-alkyl 4-aminopyrrolo[2,3-dpyrimidine derivatives related to toyocamycin, sangivamycin and thiosangivamycin have been prepared and tested for their activity against human cytomegalovirus (HCMV). Only the thioamide substituted derivatives demonstrated biological activity.

The pyrrolopyrimidine nucleosides, toyocamycin, sangivamycin, and tubercidin are isolated from the culture filtrates of 14 species of the Streptomyces. Although earlier experiments showed that the biosynthesis of the pyrrolopyrimidine nucleosides require GTP as the common precursor, there was no...

The X-ray crystal structure of sangivamycin, a potent nucleoside inhibitor of protein kinases, has been determined. Sangivamycin crystallizes from water with its purine ring in a conformation anti to its ribose sugar. Such an anti conformation has been detected in solution for sangivamycin and o...

Coupling reaction of 2-β-C-methyl-1,2,3,4-tetra-O-benzoyl-d-ribofuranose with 4-amino-6-bromo-5-cyanopyrrolo[2,3-d]pyrimidine, followed by debromination and debenzoylation, gave the 2′-β-C-methyl toyocamycin in high yield. Based on this result, a series of 2′-β-C-methyl-4-substituted toyoca...

SummaryPyrrolopyrimidine nucleosides analogs, collectively referred to as deazapurines, are an important class of structurally diverse compounds found in a wide variety of biological niches. In this report, a cluster of genes from Streptomyces rimosus (ATCC 14673) involved in production of the d...

Sangivamycin, a structural analog of adenosine and antibiotic exhibiting antitumor and antivirus activities, inhibits protein kinase C and the synthesis of both DNA and RNA. Primary effusion lymphoma (PEL) is an aggressive neoplasm caused by Kaposi’s sarcoma-associated herpesvirus (KSHV) in imm...

New analogs of the endogenous opioid agonist endomorphin-2 (EM-2, H-Tyr-Pro-Phe-Phe-NH2) have been obtained by introducing modified tyrosines at the position 1 of the sequence. For all analogs, the cis/trans conformation ratio about the tyramine-Pro amide bond, lipophilicity, receptor affinities...

Ethylhydrazine (EH) forms the complexes MX2(EH)2 (M = Co, Ni; X = Cl; M = Co, X = Br), NiBr2(EH)2(H2O) and MX2(EH) (M = Zn, Cd; X = Cl; M = Zn, X = Br). Spectroscopic evidence suggests that these all contain bridging hydrazine ligands, the cobalt and nickel complexes containing six coordinated m...

Radicals formed during oxidative metabolism of ethylhydrazine have been spin-trapped with PBN1. The trapped species has been identified as an ethyl radical by comparison of the ESR parameters of the PBN-adduct with (1) those of the analogous adduct formed during CuCl2-catalyzed oxidation of ethy...

The geometry of ethylhydrazine was studied using the ab initio gradient method at the 4–21G(N∗)//4–21G(N∗) level. Nine stable conformers and 18 conformers found as maxima along the N-N and N-C internal rotational path were refined without any geometrical constraints.

Three carbothioamide derivatives with reversible P-type photochromic properties in the solid state were synthesized in a one-step reaction. Based on the single crystal structures, the FT-IR spectra and theory calculations, the proposed photochromic mechanism was the intermolecular proton transfe...

The synthesis of a protected 1,2-bis(indolyl)ethylhydrazine bearing the full substitution pattern present in the unusual dimeric alkaloid montamine is described. A variant of the Mitsunobu reaction was used to incorporate directly the reduced azodicarboxylate into the tryptophol side chain. The ...

The conductivity and solar cell performance of metal-iodide-doped trialkylsulphonium iodides and polyiodides have been investigated as electrolytes in dye-sensitized nanocrystalline solar cells (DNSCs). Nine different metal-iodide-containing (R2R′S)I with additional iodine provided overall sola...

The regio- and diastereospecific Wagner-Meerwein-type rearrangements of the potassium cyanide adducts of camphor-derived substituted 1-bromo-N-nitrobicyclo[2.2.1]heptan-2-imines under acidic conditions have been investigated. The selective formation of bromonorbornene derivatives has been demons...

Cis-3-hexen-1-yl acetate is a significant green note flavor compound and widely used in the food and cosmetic industry. In this research, a series of solid base KOH/γ-Al2O3 have been prepared and been utilized for the synthesis of cis-3-hexen-1-yl acetate via transesterification from cis-3-hexe...

Plants synthesize specialized metabolites which possess extremely important ecological functions including direct defense, indirect defense, and signaling. The optimal defense theory (ODT) proposes that defensive metabolites are preferentially allocated to the tissues with high fitness value or ...