Dehydrooligopeptides. VII Convenient synthesis of various dehydrodi- and tripeptide esters by using N-carboxy .ALPHA.-dehydroamino acid anhydride.
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概要
- 論文の詳細を見る
The one-pot syntheses of <I>N</I>-protected <I>Δ</I><SUP>1</SUP>- and <I>Δ</I><SUP>2</SUP>-dehydrodipeptide esters by the coupling of <I>N</I>-carboxy α-dehydroamino acid anhydride (<I>Δ</I>NCA) with several kinds of C- or N-protected L-α-amino acids are described. In addition, it was found that a similar coupling of <I>Δ</I>NCA with both C- and N-protected α-amino acids also took place to give <I>Δ</I><SUP>2</SUP>-dehydrotripeptide derivatives, involving eight kinds of important C-terminal segments of antrimycins and cirratiomycins. The configurational confirmation of the α-dehydroisoleucine residue of the antibiotics is also discussed.
- 公益社団法人 日本化学会の論文
著者
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Shin Chung-gi
Laboratory Of Oraganic Chemistry Faculty Of Engineering Kanagawa University
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Yonezawa Yasuchika
Laboratory Of Oraganic Chemistry Faculty Of Engineering Kanagawa University
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Ikeda Masahiro
Laboratory of Organic Chemistry, Faculty of Technology, Kanagawa University
関連論文
- Total Synthesis of a Macrocyclic Antibiotic, Micrococcin P_1
- Total Synthesis of a Macrocyclic Antibiotic, Micrococcin P
- Convenient Synthesis of the Central 3,6-Di(2-thiazolyl)-2-(4-thiazolyl)-pyridine Skeleton of a Macrocyclic Antibiotic, GE 2270 A
- Synthesis of a Fragment A Derivative of an Antibiotic, Nosiheptide
- Total Synthesis of Antibiotic, Micrococcin P, from 2, 3, 6-Polythiazolesubstituted Pyridine Skeleton[Fragment A-C]
- Synthesis of the Central Heterocyclic Skeleton of an Antibiotic, A10255
- Useful Synthesis of 2, 3, 6-Polythiazolesubstituted Pyridine Skeleton [Fragment A-C]of Peptide Antibiotic, Micrococcin P
- Dehydrooligopeptides. XIV. Syntheses of 2-[(Z)-1-Amino-1-alken-1-yl]oxazole-4-carboxylic Acid and the Main Common Skeleton of Thiostrepton Peptide Antibiotics, A10255G and J^
- Syntheses of 2-[(1S,3S)-1-Amino-3-carboxy-3-hydroxypropyl]-thiazole-4-carboxylic Acid and the Tripeptide Skeleton of Nosiheptide Containing the Acid
- Dehydrooligopeptides. XVII. Practical Syntheses of All of the Diastereomers of N,N-Protected 2,3-Diaminobutanoic Acids from L-and D-Threonine Derivatives
- A Convenient Synthesis of Methyl 2-[2-(Amino)ethenyl-bithiazolyl] thiazoline-4-carboxylate, an Important Skeleton of Cyclothiazomycin
- Synthesis of a Common Main Skeleton of Thiostrepton Peptide Antibiotics, A 10255G and J
- Practical Synthesis of Oligodehydroalanine Derivatives by Repetition of Stepwise Elongation of Serine Derivative and β-Elimination
- Practical Synthesis of Oxazoles Incorporated in α-Dehydroamino Acid and Dehydropeptide Structures
- Convenient Syntheses of Thiazoles Incorporated with α-Dehydroamino Acid and Dehydropeptide Structures
- Total Synthesis of Bistratamides G and H from Various Kinds of ΔAla and ΔAbu-Containing Oligopeptides
- Convenient Syntheses of 3-Deoxy-D-manno-2-octulosonic Acid (KDO) and 3-Deoxy-D-glycero-D-galacto-2-nonulosonic Acid (KDN) Derivatives from D-Mannose
- Convenient Synthesis of the Main Dehydrohexapeptide Skeleton Constituting a Macrocyclic Antibiotic, Berninamycin A
- Useful Synthesis of the Main Dehydrohexapeptide Segment of a Macrocyclic Antibiotic, Berninamycin B
- Total Syntheses of Bistratamides J, E, and H from Two Types of ΔAla-Containing Oligopeptides
- Novel Synthesis of the Main Central 2,3,6-Trisubstituted Pyridine Skeleton [Fragment A-B-C] of a Macrobicyclic Antibiotic, Cyclothiazomycin
- Convenient Synthesis of a Central 2,3,6-Trisubstituted Pyridine Skeleton of a Macrobicyclic Antibiotic, Cyclothiazomycin
- Useful Synthesis of Fragment A-C-D of a Thiostrepton-type Macrocyclic Antibiotic, Thiocilline I
- Total Synthesis of Bistratamide G, a Metabolite of the Philippines Ascidian Lissoclinum bistratum, from Dehydrotripeptides
- Convenient Synthesis of the Main Tridehydropentapeptide Skeleton for a Macrocyclic Antibiotic, Sulfomycin I
- Asymmetric Synthesis of the Main Pyridine Skeleton for a Macrobicyclic Antibiotic, Cyclothiazomycin
- Convenient Synthesis of (3S, 5S)-5-Hydroxy- and (3R, 5S)-5-Chloropiperazic Acids of a Peptide Antibiotic, Monamycin G^3
- Dehydrooligopeptides. XX. Unusual Peptide Bond Cleavage of Dehydrotripeptide Esters Containing α-Dehydroamino Acid Residue at P_2 by Using Papain
- Dehydrooligopeptides. XVIII. Enzymatic Hydrolysis and Coupling of Dehydrodipeptide Esters Containing α-Dehydroamino Acid Residue by Using Papain
- Convenient Synthesis of Dehydrooligopeptides Containing α-Dehydroamino Acid Residue Alone
- Facile Syntheses of (s, s)-2, 3-Diaminobutyric Acid and the Acid Containing N-Terminal Tripeptide of Antrimycins
- α,β-Unsaturated Carboxylic Acid Derivatives. IV. General Synthesis of Unsaturated Unsymmetric 3,6-Disubstituted-2,5-piperazinediones
- Dehydrooligopeptides. XIII. Selective Enzymatic Hydrolysis of N-Protected .ALPHA.-Dehydroglutamic Acid Diesters and Their Analogs Using Papain as Catalyst.
- Dehydrooligopeptides. X. Useful synthetic method for (E)- and (Z)-isomers of dehydroaspartic acids, and their .DELTA.1,2-dehydrodipeptides by the base-catalyzed .BETA.-elimination.
- The synthesis and reaction of spiro(oxolane-2,2'-piperazine)-3',6'-diones with N-bromosuccinimide in the presence or absence of water.
- Synthesis of (3Z, 6E)-1-N-Methylalbonoursin, a New Metabolite from Streptomyces albus
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- .ALPHA.,.BETA.-Unsaturated carboxylic acid derivatives. XIII. The synthesis and configuration of alkyl 2-acylamino-2-alkenoates and their cyclized 2,5-piperazinedione derivatives.
- Dehydrooligopeptides. XI. Facile syntheses of various kinds of dehydrodi- and tripeptides, and dehydroenkephalins containing .DELTA.Tyr residue by using N-carboxydehydrotyrosine anhydride.
- Dehydrooligopeptides. IX. Syntheses and conversions of .ALPHA.-dehydroglutamine derivatives to N-carboxy-.ALPHA.-dehydroglutamine anhydride and .DELTA.1-dehydroglutaminyldipeptides.
- Dehydrooligopeptides. III. Synthesis of (Z,Z)- and (Z,E)-geometric isomers of dehydrodipeptides and their base-catalyzed transformation to the hydantoin derivatives.
- The confirmation of the configuration of ethyl 2-bromo-3-nitro-2-alkenoate by 13C NMR spectroscopy.
- Dehydrooligopeptides. VI Facile transformation of .ALPHA.-phosphoranylideneamino-.ALPHA.-alkenoates to .DELTA.2-dehydrodipeptide derivatives.
- Dehydrooligopeptides. VII Convenient synthesis of various dehydrodi- and tripeptide esters by using N-carboxy .ALPHA.-dehydroamino acid anhydride.
- .ALPHA.,.BETA.-Unsaturated carboxylic acid derivatives. XVII. The facile synthesis of ethyl .ALPHA.-azido-.ALPHA.-alkenoates and reduction to ethyl .ALPHA.-amino-.ALPHA.-alkenoates.
- .ALPHA.,.BETA.-Unsaturated carboxylic acid derivatives. XIV. The synthesis and reduction of Diels-Alder adducts from ethyl 3-nitro-2-alkenoates and cyclopentadiene.
- .ALPHA.,.BETA.-Unsaturated carboxylic acid derivatives. XV. The reaction of ethyl 3-nitro-2-alkenoate with bromine azide or bromine, and transformations of the products.
- .ALPHA.,.BETA.-Unsaturated carboxylic acid derivatives. XXI. A novel synthesis of .ALPHA.-dehydroamino acid derivatives by the Arbusov reaction of .ALPHA.-phosphoranylideneamino-2-alkenoates.
- Dehydrooligopeptides. II. The synthesis of dehydrodehydrodipeptides by direct coupling and base-catalyzed .BETA.-elimination.
- Convenient Synthesis of Dehydrooligopeptides by the Solid Phase Method Using N-Carboxy α-Dehydroamino Acid Anhydride
- A Novel Synthesis of Ethyl β-Diethoxyphosphinyl-α,β-unsaturated-carboxylates
- The formation of the main skelton of bicyclomycin by the cyclization of 6-hydroxy-3-(3-hydroxypropyl)-2,5-piperazinedione derivatives.
- The Synthesis and Reaction of α,β-Unsaturated α-Nitrocarboxylic Esters
- .ALPHA.,.BETA.-Unsaturated carboxylic acid derivatives. XIX. The convenient synthesis of .ALPHA.-alkoxy-, .ALPHA.-hydroxy-.ALPHA.-amino acid, and its cyclic dipeptide from .ALPHA.-dehydroamino acid.
- α,β-Unsaturated Carboxylic Acid Derivatives. X. The Synthesis and Reaction of α-Azido-diethoxyphosphinyl-α- and β-alkenes
- Studies on Nitro Carboxylic Acids. III. The Reaction of α-Nitroolefins with Triethyl or Diethyl Phosphite