- ENANTIOSPECIFIC SYNTHESIS OF D-α,ω-DIAMINOALKANOIC ACIDS
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An enantiospecific synthesis of D-Nω-Boc-α, ω-diaminoalkanoic acids starting from L-serine is described.
- Beaulieu, Pierre L.,Schiller, Peter W.
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- Comparison of N-terminal modifications on neurotensin(8-13) analogues correlates peptidestability but not binding affinity with in vivo efficacy
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Neurotensin(8-13) and two related analogues were used as model systems to directly compare various N-terminal peptide modifications representing both commonly used and novel capping groups. Each N-terminal modification prevented aminopeptidase cleavage but surprisingly differed in its ability to inhibit cleavage at other sites, a phenomenon attributed to long-range conformational effects. None of the capping groups were inherently detrimental to human neurotensin receptor 1 (hNTR1) binding affinity or receptor agonism. Although the most stable peptides exhibited the lowest binding affinities and were the least potent receptor agonists, they produced the largest in vivo effects. Of the parameters studied only stability significantly correlated with in vivo efficacy, demonstrating that a reduction in binding affinity at NTR1 can be countered by increased in vivo stability.
- Orwig, Kevin S.,Lassetter, McKensie R.,Hadden, M. Kyle,Dix, Thomas A.
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- Synthesis method of double different protected amino acids
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The invention relates to a synthesis method of double different protected amino acids.The technical problems of harsh reaction conditions, inapplicability of production enlarging and the like in an existing synthesis method are mainly solved. According to the technical scheme, the synthesis method of double different protected amino acids comprises the following steps: one of Boc20, Alloc-Cl or Cbz-Osuis added to amino alcohol under the action of an alkaline reagent to obtain a compound 1; the compound 1 reacts with methanesulfonyl chloride or paratoluensulfonyl chloride to obtain an intermediate, then a halide is added into acetone, heating and refluxing are executed to obtain a compound 2; the compound 2 is condensed with diethyl acetamidomalonate under the action of an alkaline agent togenerate a compound 3; the compound 3 is dissolved in alcohol and water, an inorganic base is added, heating, hydrolyzing and decarboxylating are executed to obtain a compound 4; acetylase is added into deionized water to obtain a compound 5 through enzymolysis; amino acid protection is executed, wherein one of Fmoc-Osu, Cbz-OSu, Alloc-Cl or Boc20 is added into thecompound 5 under the action of an alkaline agent to generatea target compound A.
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- Asymmetric synthesis of non-natural homologues of lysine
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A series of non-natural amino acid homologues of L- and D-lysine have been synthesized and protected for use in solid-phase peptide synthesis. With these residues, electrostatics and hydrophobicity of peptides can be enhanced or altered.
- Kennedy, Kevin J.,Lundquist IV, Joseph T.,Simandan, Tiberiu L.,Beeson, Craig C.,Dix, Thomas A.
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p. 1937 - 1940
(2007/10/03)
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