BIOMAT Database Logo BIOMAT Database Logo

Cyclic peptides. XIV. Syntheses of [4-l-leucine]-, [4-D-leucine]-, and [3-L-proline, 4-D-leucine]-Cyl-2. 1982

A Yasutake, and H Aoyagi, and I Sada, and T Kato, and N Izumiya

Cyl-2 is a phytotoxic cyclic tetrapeptide with the sequence of cyclo(D-Tyr(Me)-L-Ile-L-Pip-Aoe-): Aoe, 2-amino-8-oxo-9,10-epoxydecanoic acid. The configuration of Aoe is unknown. Three analogs, cyclo(-D-Try(Me)-L-Ile-L-Pip-L(and D)-Leu-) (1 and 2) and cyclo(-D-Tyr(Me)-L-Ile-L-Pro-D-Leu-) (3), were synthesized and spectroscopic features of these analogs were compared. 1H-N.m.r. spectra of cyclo(D-Tyr(Me)-L-Ile-L-Pip-L-Leu) (1), cyclo(-D-Tyr(Me)-L-Ile-L-Pro-L-Leu-) (4), and Cyl-2 showed a similar pattern. On the other hand, the spectra of analogs 2 and 3 showed a different pattern, the Ile-Pro bond in 3 being in cis conformation.

UI MeSH Term Description Entries
D007202 Indicators and Reagents Substances used for the detection, identification, analysis, etc. of chemical, biological, or pathologic processes or conditions. Indicators are substances that change in physical appearance, e.g., color, at or approaching the endpoint of a chemical titration, e.g., on the passage between acidity and alkalinity. Reagents are substances used for the detection or determination of another substance by chemical or microscopical means, especially analysis. Types of reagents are precipitants, solvents, oxidizers, reducers, fluxes, and colorimetric reagents. (From Grant & Hackh's Chemical Dictionary, 5th ed, p301, p499) Indicator,Reagent,Reagents,Indicators,Reagents and Indicators
D009682 Magnetic Resonance Spectroscopy Spectroscopic method of measuring the magnetic moment of elementary particles such as atomic nuclei, protons or electrons. It is employed in clinical applications such as NMR Tomography (MAGNETIC RESONANCE IMAGING). In Vivo NMR Spectroscopy,MR Spectroscopy,Magnetic Resonance,NMR Spectroscopy,NMR Spectroscopy, In Vivo,Nuclear Magnetic Resonance,Spectroscopy, Magnetic Resonance,Spectroscopy, NMR,Spectroscopy, Nuclear Magnetic Resonance,Magnetic Resonance Spectroscopies,Magnetic Resonance, Nuclear,NMR Spectroscopies,Resonance Spectroscopy, Magnetic,Resonance, Magnetic,Resonance, Nuclear Magnetic,Spectroscopies, NMR,Spectroscopy, MR
D009904 Optical Rotation The rotation of linearly polarized light as it passes through various media. Optical Activity,Activity, Optical,Rotation, Optical
D010456 Peptides, Cyclic Peptides whose amino acid residues are linked together forming a circular chain. Some of them are ANTI-INFECTIVE AGENTS; some are biosynthesized non-ribosomally (PEPTIDE BIOSYNTHESIS, NON-RIBOSOMAL). Circular Peptide,Cyclic Peptide,Cyclic Peptides,Cyclopeptide,Orbitide,Circular Peptides,Cyclopeptides,Orbitides,Peptide, Circular,Peptide, Cyclic,Peptides, Circular
D013329 Structure-Activity Relationship The relationship between the chemical structure of a compound and its biological or pharmacological activity. Compounds are often classed together because they have structural characteristics in common including shape, size, stereochemical arrangement, and distribution of functional groups. Relationship, Structure-Activity,Relationships, Structure-Activity,Structure Activity Relationship,Structure-Activity Relationships

Related Publications

A Yasutake, and H Aoyagi, and I Sada, and T Kato, and N Izumiya
Conformational transitions of cyclic D,L-peptides.
April 2009, Journal of computational chemistry,
A Yasutake, and H Aoyagi, and I Sada, and T Kato, and N Izumiya
Conformational studies of cyclic enkephalin analogues with L- or D-proline in position 3.
April 2002, Biopolymers,
A Yasutake, and H Aoyagi, and I Sada, and T Kato, and N Izumiya
The structure of viscosin, a peptide antibiotic. I. Syntheses of D- and L-3-hydroxyacyl-L-leucine hydrazides related to viscosin.
July 1971, Chemical & pharmaceutical bulletin,
A Yasutake, and H Aoyagi, and I Sada, and T Kato, and N Izumiya
Cyclic peptides of sarcosine. Syntheses and conformation.
January 1975, Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry,
A Yasutake, and H Aoyagi, and I Sada, and T Kato, and N Izumiya
Conformational studies of peptides containing cis-3-hydroxy-D-proline.
October 2004, The Journal of organic chemistry,
A Yasutake, and H Aoyagi, and I Sada, and T Kato, and N Izumiya
Syntheses of the 3- and 4-thio analogues of 4-nitrophenyl 2-acetamido-2-deoxy-beta-D-gluco- and galactopyranoside.
November 2007, Carbohydrate research,
A Yasutake, and H Aoyagi, and I Sada, and T Kato, and N Izumiya
Tertiary peptide bond containing-oligo(Leu)s. Conformational studies in solution of oligo (L-leucine)s with L-proline residue and glycyl-N-(2, 4-dimethoxybenzyl)-L-leucine sequence.
July 1984, International journal of peptide and protein research,
A Yasutake, and H Aoyagi, and I Sada, and T Kato, and N Izumiya
Synthesis of 3'-fluoro-2',3'-dideoxy-2',3'-didehydro-4'-ethynyl-D- and -L-furanosyl nucleosides.
September 2004, The Journal of organic chemistry,
A Yasutake, and H Aoyagi, and I Sada, and T Kato, and N Izumiya
Enantiomeric syntheses of conformationally restricted D- and L-2', 3'-dideoxy-2',3'-endo-methylene nucleosides from carbohydrate chiral templates.
February 2000, The Journal of organic chemistry,
A Yasutake, and H Aoyagi, and I Sada, and T Kato, and N Izumiya
Syntheses of methyl (4,6-dideoxy-alpha-L-lyxo-hexopyranosyl)-(1-->3)- and (4-deoxy-4-fluoro-alpha-L-rhamnopyranosyl)-(1-->3)- 2-acetamido-2-deoxy-alpha-D-glucopyranosides, analogs of the mycobacterial arabinogalactan linkage disaccharide.
November 1999, Carbohydrate research,
Copied contents to your clipboard!