An experimental approach to long-lasting hypotensive eledoisin-like peptides

Bernardi, L.; Castiglione, Roberto; Fregnan, G. B.; Glässer, A.

doi:10.1111/j.2042-7158.1967.tb08043.x

Cited by 12 publications

(15 citation statements)

References 7 publications

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“…The residue was dissolved in a mixture of 1 mL of H 2 O and 2 mL of CF 3 CO 2 H and evaporated to dryness again after 30 min. The product was purified by recrystallization from EtOH, , yield 60%: 1 H NMR (D 2 O) δ 1.38 (m, 2H, γ -C H 2 ), 1.59 (m, 2H, β -C H 2 ), 1.88 (m, 2H, δ -C H 2 ), 3.22 (t, 2H, ε -C H 2 ), 3.70 (t, 1H, α -C H ), 6.26 (s, 1H, Cl 2 C H ); MS, m / z 258.22 (MH + ).…”

Section: Methodsmentioning

confidence: 99%

Mechanism of Aqueous Decomposition of Trichloroethylene Oxide

and

Guengerich

1999

J. Am. Chem. Soc.

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The aqueous decomposition of trichloroethylene (TCE) oxide is shown to involve both pH-independent and hydronium ion-dependent regions. C−C bond scission is a major reaction at all pH values. Disappearance of TCE oxide is the rate-determining step for the formation of CO under the conditions studied. The product distribution of CO and three carboxylic acids (HCO2H, Cl2CHCO2H, and glyoxylic acid) did not change considerably over the pH range of −1.5−14, in general, even though the hydrolysis mechanism changes from hydronium ion-dependent to pH-independent. Mechanisms for the hydronium ion-dependent and pH-independent hydrolysis of TCE oxide were elucidated on the basis of the results of H2 18O and H incorporation and identification of products of the reaction of TCE oxide with lysine in both H2 16O and H2 18O. In the pH-independent hydrolysis, a zwitterionic intermediate could be formed and undergo an intramolecular rearrangement (Cl- shift) to generate dichloroacetyl chloride, which would subsequently decompose to Cl2CHCO2H. The zwitterionic intermediate could also hydrolyze at the less sterically hindered methylene to give a glycol anion, which would dehydrohalogenate to form an oxoacetyl chloride intermediate. The oxoacetyl chloride could hydrolyze to generate either glyoxylic acid, as a final product, or an anionic intermediate, which could go through a concerted mechanism to generate CO, HCO2H, and chloride. A mechanism proposed for the hydronium ion-dependent hydrolysis is very similar to that for the pH-independent hydrolysis except for the first step, which involves hydronium ion attack on TCE oxide to form a TCE-oxide cation intermediate. The lysine amide adducts were characterized by HPLC and mass spectrometry as those resulting from reaction with the postulated acyl chlorides.

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Section: Methodsmentioning

confidence: 99%

Mechanism of Aqueous Decomposition of Trichloroethylene Oxide

and

Guengerich

1999

J. Am. Chem. Soc.

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“…13 (S)-2-Benzyloxycarbonylamino-6-propionylamino-hexanoic Acid (4b). Compound 4b was synthesized by method A from Z-Lys (2.8 g, 10 mmol) and propionyl chloride (0.87 mL, 10 mmol).…”

Section: Methodsmentioning

confidence: 99%

“…The resulting product was chromatographed with ethyl acetate/nhexane (2:1 [1-(4-Methyl-2-oxo-2H-chromen-7-ylcarbamoyl)-5-(2,2,2-trifluoroacetylamino) 10 (m, 1H), 3.15-3.14 (m, 2H), 2.38 (s, 3H), 1.66-1.31 (m, 6H). 13 (R)-6-Acetylamino-2-benzyloxycarbonylamino-hexanoic Acid (6). 26 (m, 13H).…”

Section: S)-[5-butyrylamino-1-(4-methyl-2-oxo-2h-chromen-7-ylcarbamoymentioning

confidence: 99%

“…26 (m, 13H). 13 (S)-{4-Acetylamino-1-[(4-methyl-2-oxo-2H-chromen-7-ylcarbamoyl)methyl]butyl}carbamic Acid Benzyl Ester (10). Compound 9 (0.32 g, 0.60 mmol) was dissolved in a mixture of trifluoroacetic acid in dichloromethane (1:1, 4 mL).…”

Section: S)-[5-butyrylamino-1-(4-methyl-2-oxo-2h-chromen-7-ylcarbamoymentioning

confidence: 99%

“…Acyl chlorides and NaOH were used for the other acyl substituents. 13 In the synthesis of the -analogue 10, the coumarin was coupled first to an -Boc-protected -Z-lysine and was -acetylated in the last step after cleavage of the Boc group (Figure 1). Substrate Reactivity.…”

Section: Synthesismentioning

confidence: 99%

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Subtype Selective Substrates for Histone Deacetylases

et al. 2004

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To probe the steric requirements for deacylation, we synthesized lysine-derived small molecule substrates and examined structure-reactivity relationships with various histone deacetylases. Rat liver, human HeLa, and human recombinant class I and II histone deacetylases (HDACs) as well as human recombinant NAD + -dependent SIRT1 (class III enzyme) were used in these studies. A benzyloxycarbonyl substituent on the R-amino group yielded the highest conversion rates. Replacing the -acetyl group with larger lipophilic acyl substituents led to a pronounced decrease in conversion by class I and II enzymes; the class III enzyme displayed a greater tolerance. Incubations with recombinant FLAG-tagged human HDACs 1, 3, and 6 showed a distinct subtype selectivity among small molecule substrates. The subtype selectivity of HDAC inhibitors could be predicted with these substrates and an easily obtainable mixture of HDAC subtypes.

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