Amino acids and peptides. XIII. Synthetic studies on N-terminal tripeptide amide analogs of fibrin alpha-chain

N-Terminal tripeptide analogs of fibrin alpha-chain were synthesized and their inhibitory effect on fibrinogen/thrombin clotting was examined. A new water-soluble active ester, 3-pyridinium ester, was used for the synthesis. Among the synthetic peptides, H-Gly-Pro-Arg-hexamethyleneimine exhibited the highest inhibitory effect on fibrinogen-thrombin clotting.     

Two‐stage copolycondensation of preformed oligomers with bisphenols by tosyl chloride/dimethylformamide/pyridine from distributions of resulting oligomers determined by a combination of gel permeation chromatography and NMR

A two‐stage co‐oligomerization of the oligomers initially formed from an equimolar mixture of isophthalic acid (IPA) and terephthalic acid (TPA) and 2,2‐bis(4‐hydroxyphenyl)propane (BPA, 50 mol %) with bisphenols (BPs, 20 mol %) was carried out using a tosyl chloride/dimethylformamide/pyridine condensing agent. The distributions of the resulting oligomers (n_x‐mers), which were quenched with methanol, were determined by a combination of gel permeation chromatography (GPC) and NMR. These distributions (presented by molar percentage) were conveniently calculated with the equation n_x (mol %) = n_x (% mol by GPC) × n₀ (mol % by NMR)/n₀ (% mol by GPC), where n_x (% mol) = n_x (wt % by GPC)/its molecular weight. The results showed the distributions of the preformed IPA/TPA‐BPA oligomers to be in fairly good accord with those obtained directly from GPC and to be supported by the NMR results. The calculation was applied to the co‐oligomers prepared up to a reaction of 0.7, at which there was an increase in the number of higher oligomers indivisible by GPC and the distributions could no longer be determined by molar percentage. The calculated distributions are discussed in relation to the results of copolycondensation. The sequence distributions in the resulting co‐oligomers, which were also examined by NMR, are compared with those in the copolymers. © 2003 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 42: 44–51, 2004     

Microwave-promoted Suzuki-Miyaura coupling reactions in a cycloalkane-based thermomorphic biphasic system

Microwave-promoted Suzuki-Miyaura coupling reaction of aryl halides attached to a cycloalkane-soluble platform was accomplished in a cycloalkane-based thermomorphic biphasic system. Following irradiation and subsequent cooling, the monophasic reaction mixture immediately formed a biphasic solution to allow facile workup and separation of the product.     

Inclusion behavior of thiacalix[4]arenetetrasulfonate toward water-miscible organic molecules studied by salting-out and X-ray crystallography

[reaction: see text] Inclusion ability of thiacalix[4]arenetetrasulfonate (TCAS) toward water-miscible organic molecules such as alcohols, ketones, cyclic ethers, and so on was studied by salting-out of the inclusion complex. NMR spectra of the recovered precipitates showed size selectivity to include the guest molecules. X-ray crystallographic analyses of TCAS salts including acetone and 1,4-dioxane suggested that guests are retained with the aid of cation coordination and H-bonding.     

Formation of pyrazine derivatives from D-glucosamine and their deoxyribonucleic acid (DNA) strand breakage activity

Two pyrazine derivatives [fructosazine (3) and deoxyfructosazine (6)] were simultaneously formed in a solution of D-glucosamine hydrochloride under various conditions. They showed deoxyribonucleic acid (DNA) strand breakage activity in plasmid pBR322 comparable to that of D-glucosamine. The DNA strand breakage by fructosazine (3) was stimulated by Cu2+.     

A new method for the evaluation of the relative stability of organosulfur radicals by competitive elimination technique

The relative stability of various organosulfur radicals is estimated by competitive elimination technique using tributyltin radical and acetophenone derivatives having two different sulfur substituents at α and α positions.     

Application of 1,2,3,5,6,7-hexahydropyrrolizinium perchlorate in the synthesis of 7a-substituted hexahydro-1h-pyrrolizines

The method for preparing 7a-substituted hexahydro-1H-pyrrolizines 2 from 1,2,3,5,6,7-hexahydropyrrol-izinium Perchlorate (3) was investigated, by which introduction of a wide variety of functionalities on C(7a) could be achieved easily.     

Stereoselective synthesis of all stereoisomers of vicinal and distal bis(O-2-aminoethyl)-p-tert-butylthiacalix[4]arene

O,O″- and O,O′-bis(2-aminoethyl)-p-tert-butylthiacalix[4]arenes of anti conformation have been prepared by the reduction of the corresponding O,O″- and O,O′-bis(cyanomethyl) ethers. Their syn-O,O″- and O,O′-counterparts have been prepared by alternative routes via the Mitsunobu reaction of thiacalix[4]arene with N-(2-hydroxyethyl)phthalimide and the reduction of a O,O′-disiloxanediyl-bridged O″,O?-bis(cyanomethyl) ether of 1,2-alternate conformation, respectively. These products are expected to serve as useful precursors of highly elaborated synthetic receptors, including biscalixarenes.