Dehydrooligopeptides. XIII. Selective Enzymatic Hydrolysis of N-Protected .ALPHA.-Dehydroglutamic Acid Diesters and Their Analogs Using Papain as Catalyst.
スポンサーリンク
概要
- 論文の詳細を見る
Since the α-ester of α,γ-dimethyl <I>N</I>-benzyloxycarbonyl-α-dehydroglutamate (<I>Δ</I>Glu) was found to be hydrolyzed using papain, a variety of <I>N</I>-protected α-dehydroglutamates and their analogs, both esters of which were the same or different from each other, were newly synthesized and subjected to a similar hydrolysis. Although the substrates, with bulkier ester group at the γ- as well as α-positions, were found to become difficult to hydrolyze, the kind and size of the <I>N</I>-protecting group did not effect the hydrolysis. Moreover, it was found that the length of side chain of the substrate greatly influenced hydrolysis. The present study suggests that papain may become a useful tool for the hydrolysis and coupling of <I>Δ</I>Glu with α-amino acid or peptide.
- 公益社団法人 日本化学会の論文
著者
-
Shin Chung-gi
Laboratory Of Oraganic Chemistry Faculty Of Engineering Kanagawa University
-
Seki Masashi
Laboratory Of Organic Chemistry Faculty Of Technology Kanagawa University
-
Takahashi Nobuyuki
Laboratory For Molecular Function Of Food Division Of Food Science And Biotechnology Graduate School
関連論文
- ISOLATION OF BRASSINOSTEROID DEFICIENCY-INSENSITIVE MUTANTS OF ARABIDOPSIS
- DEVELOPMENT OF SELECTIVE AND POTENT BRASSINOSTEROID BIOSYNTHESIS INHIBITORS AND ISOLATION OF INHIBITOR INSENSITIVE MUTANTS OF ARABIDOPSIS
- Development of series of gateway binary vectors, pGWBs, for realizing efficient construction of fusion genes for plant transformation
- Gateway vectors for plant transformation
- 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
- Cloning and Sequencing Analysis of Alginate Lyase Genes from the Marine Bacterium Vibrio sp. O2
- Effects of Fucoidan from Mozuku on Human Stomach Cell Lines
- Genetic Analysis of chs1^+ and chs2^+ Encoding Chitin Synthases from Schizosaccharomyces pombe
- POSSIBLE ROLE OF CND41 IN DEGRADATION OF RUBISCO
- Functinal analysis of cig (cytokinin inducible gene)
- Total Synthesis of Bistratamides G and H from Various Kinds of ΔAla and ΔAbu-Containing Oligopeptides
- Convenient Synthesis of the Main Dehydrohexapeptide Skeleton Constituting a Macrocyclic Antibiotic, Berninamycin A
- Inhibitory Effect of Monoacylglycerol on Fatty Acid Uptake into Rat Intestinal Epithelial Cells
- Oleyl Alcohol Inhibits Intestinal Long-Chain Fatty Acid Absorption in Rats
- Two Glutamic Acids in Chitosanase A from Matsuebacter chitosanotabidus 3001 Are the Catalytically Important Residues
- 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
- The Arabidopsis FLAKY POLLEN1 Gene Encodes a 3-Hydroxy-3-Methylglutaryl-Coenzyme A Synthase Required for Development of Tapetum-Specific Organelles and Fertility of Pollen Grains
- Development of R4 Gateway Binary Vectors (R4pGWB) Enabling High-Throughput Promoter Swapping for Plant Research
- Improved Gateway Binary Vectors : High-Performance Vectors for Creation of Fusion Constructs in Transgenic Analysis of Plants
- Development of Gateway Binary Vectors, R4L1pGWBs, for Promoter Analysis in Higher Plants
- Feedback-Regulation of Strigolactone Biosynthetic Genes and Strigolactone-Regulated Genes in Arabidopsis
- Development of a Novel PPARγ Ligand Screening System Using Pinpoint Fluorescence-Probed Protein
- Gateway Binary Vectors with the Bialaphos Resistance Gene, bar, as a Selection Marker for Plant Transformation
- Life history and migration of Sakhalin taimen, Hucho perryi, caught from Lake Akkeshi in eastern Hokkaido, Japan, as revealed by Sr:Ca ratios of otoliths
- Development of a Series of Gateway Binary Vectors Possessing a Tunicamycin Resistance Gene as a Marker for the Transformation of Arabidopsis thaliana
- Soymorphin-5, a soy-derived μ opioid peptide, improves glucose and lipid metabolism in diabetic KK-Ay mice
- Surface Melting of an n-Alkane Crystallite
- Comparative and Stability Analyses of 9- and 13-Oxo-octadecadienoic Acids in Various Species of Tomato
- A Method for the Simultaneous Determination of 3T3-L1 Adipocyte Metabolites by Liquid Chromatography/Mass Spectrometry Using [^C]-stable Isotopes
- An in Vitro Analysis System Using a Fluorescence Protein Reporter for Evaluating Anti-Inflammatory Effects in Macrophages
- Two Sec13p Homologs, AtSec13A and AtSec13B, Redundantly Contribute to the Formation of COPII Transport Vesicles in Arabidopsis thaliana
- Facile Syntheses of (s, s)-2, 3-Diaminobutyric Acid and the Acid Containing N-Terminal Tripeptide of Antrimycins
- Expression Analysis of Arabidopsis thaliana Small Secreted Protein Genes
- 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
- Long-Chain Free Fatty Acid Profiling Analysis by Liquid Chromatography–Mass Spectrometry in Mouse Treated with Peroxisome Proliferator-Activated Receptor α Agonist
- Dehydrooligopeptides. VIII. Convenient syntheses of various dehydrotyrosine derivatives protected with useful N,O-protecting groups via N-carboxy dehydrotyrosine anhydrides.
- .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.
- Evaluation of canine T-cell dependent antibody response to the primary and secondary immunization with keyhole limpet hemocyanin