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Systematic benchmarking of 13 AI methods for predicting cyclic peptide membrane permeability. [PDF]
Liu W, Li J, Verma CS, Lee HK.
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International Journal of Peptide and Protein Research, 1986
In order to investigate the role of the L‐2‐hydroxy‐3‐methylbutanoic acid residue at position 2 of AM‐toxin I (cyclic tetradepsipeptide) on necrotic activity for apple leaves, two analogs, [L‐lactic acid2] AM‐toxin I and [L‐2‐hydroxy‐4‐methylpentanoic acid2] AM‐toxin I, were synthesized by the conventional method for peptide synthesis.
HISAKAZU MIHARA +6 more
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In order to investigate the role of the L‐2‐hydroxy‐3‐methylbutanoic acid residue at position 2 of AM‐toxin I (cyclic tetradepsipeptide) on necrotic activity for apple leaves, two analogs, [L‐lactic acid2] AM‐toxin I and [L‐2‐hydroxy‐4‐methylpentanoic acid2] AM‐toxin I, were synthesized by the conventional method for peptide synthesis.
HISAKAZU MIHARA +6 more
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International Journal of Peptide and Protein Research, 1985
cyclo(‐l‐Pro‐l‐Val‐l‐Pro‐l‐Val‐) (1L) and cyclo(‐l‐Pro‐d‐Val‐l‐Pro‐d‐Val‐) (1D) were synthesized by the conventional method for peptide synthesis. Conformations of 1L and 1D in solution were studied. Compound 1L has a cis‐trans‐cis‐trans backbone conformation with C2 symmetry in CDCl3.
TOSHIHISA UEDA +3 more
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cyclo(‐l‐Pro‐l‐Val‐l‐Pro‐l‐Val‐) (1L) and cyclo(‐l‐Pro‐d‐Val‐l‐Pro‐d‐Val‐) (1D) were synthesized by the conventional method for peptide synthesis. Conformations of 1L and 1D in solution were studied. Compound 1L has a cis‐trans‐cis‐trans backbone conformation with C2 symmetry in CDCl3.
TOSHIHISA UEDA +3 more
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International Journal of Peptide and Protein Research, 1980
Å number of cyclo (Δaminoacyl‐L‐aminoacyl) (Δaminoacyl =ΔAba, ΔVal, ΔLeu, ΔApp, ΔPhe and ΔTrp; L‐aminoacyl=L‐Ala, L‐Val, L‐Leu and L‐Lys (e‐Ac)) were synthesized by the condensation of cyclo (N‐acetyl‐Gly‐N‐acetyl‐L‐aminoacyl) with corresponding aldehyde or acetone and subsequent treatment with hydrazine. Each cyclo (Δaminoacyl‐L‐aminoacyl) except ones
TATSUHIKO KANMERA +3 more
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Å number of cyclo (Δaminoacyl‐L‐aminoacyl) (Δaminoacyl =ΔAba, ΔVal, ΔLeu, ΔApp, ΔPhe and ΔTrp; L‐aminoacyl=L‐Ala, L‐Val, L‐Leu and L‐Lys (e‐Ac)) were synthesized by the condensation of cyclo (N‐acetyl‐Gly‐N‐acetyl‐L‐aminoacyl) with corresponding aldehyde or acetone and subsequent treatment with hydrazine. Each cyclo (Δaminoacyl‐L‐aminoacyl) except ones
TATSUHIKO KANMERA +3 more
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International Journal of Peptide and Protein Research, 1984
In order to explore the route for cyclization of linear oligopeptide containing a ΔAla (α, β‐dehydroalanine) residue, AM‐toxin II was synthesized. As a preliminary experiment, synthesis of [L‐Phe3] AM‐toxin II, containing L‐Phe in place of L‐App (L‐2‐amino‐5‐phenylpentanoic acid), was attempted.
TOSHIRO KOZONO +4 more
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In order to explore the route for cyclization of linear oligopeptide containing a ΔAla (α, β‐dehydroalanine) residue, AM‐toxin II was synthesized. As a preliminary experiment, synthesis of [L‐Phe3] AM‐toxin II, containing L‐Phe in place of L‐App (L‐2‐amino‐5‐phenylpentanoic acid), was attempted.
TOSHIRO KOZONO +4 more
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International Journal of Peptide and Protein Research, 1981
In order to establish possible routes for the synthesis of AM‐toxins, cyclotetradepsipeptides containing Dha, Pyr‐L‐Ala‐L‐Hmb‐L‐Tyr‐NH2 were prepared and treated with TFA or anhydrous HF. The product was identified to be cyclo (‐α‐Hyala‐L‐Ala‐L‐Hmb‐L‐Tyr‐), resulting from intramolecular condensation of the α‐keto and amide group with the formation of ...
Kosaku Noda +4 more
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In order to establish possible routes for the synthesis of AM‐toxins, cyclotetradepsipeptides containing Dha, Pyr‐L‐Ala‐L‐Hmb‐L‐Tyr‐NH2 were prepared and treated with TFA or anhydrous HF. The product was identified to be cyclo (‐α‐Hyala‐L‐Ala‐L‐Hmb‐L‐Tyr‐), resulting from intramolecular condensation of the α‐keto and amide group with the formation of ...
Kosaku Noda +4 more
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Orally Absorbed Cyclic Peptides
Chemical Reviews, 2017Peptides and proteins are not orally bioavailable in mammals, although a few peptides are intestinally absorbed in small amounts. Polypeptides are generally too large and polar to passively diffuse through lipid membranes, while most known active transport mechanisms facilitate cell uptake of only very small peptides. Systematic evaluations of peptides
Daniel S. Nielsen +5 more
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Journal of the American Chemical Society, 2006
The synthesis of rotaxanes derived from the synthetic peptide macrocycles cyclo(l-ProGly)4 and cyclo(l-ProGly)5 and diammonium threads is described. [2]Rotaxanes are formed in good yields (56-63%), despite the disruption of internal amide-amide hydrogen bonding in the macrocycles.
Vincent, Aucagne +3 more
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The synthesis of rotaxanes derived from the synthetic peptide macrocycles cyclo(l-ProGly)4 and cyclo(l-ProGly)5 and diammonium threads is described. [2]Rotaxanes are formed in good yields (56-63%), despite the disruption of internal amide-amide hydrogen bonding in the macrocycles.
Vincent, Aucagne +3 more
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Studies on cyclic peptides. II. Synthesis of cyclic peptides containing sarcosine
Biopolymers, 1975AbstractCyclic peptides containing sarcosine, cyclo‐(Pro‐Sar‐Gly)2, cyclo‐(Sar‐Sar‐Gly)2, cyclo‐(Sar4), and cyclo‐(Sar6) have been synthesized by the cyclization of the p‐nitrophenyl ester of linear peptides. The tert‐butoxycarbonyl group was used as the Nα‐protecting group, which was removed by acid.
T, Sugihara, Y, Imanishi, T, Higashimura
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