Amino-acids and peptides. Part XIII. Syntheses of two fourteen-membered ring cyclotetrapeptides

Author(s):  
C. H. Hassall ◽  
D. G. Sanger ◽  
B. K. Handa
Keyword(s):  
2019 ◽  
Author(s):  
Clara M. Agapie ◽  
Melissa Sampson ◽  
William Gee

The work describes a new chemical means of visualising latent fingerprints (fingermarks) using tropolone. Tropolone reacts with amino acids within the fingermark residue to form adducts that absorb UV radiation. These adducts provide useful contrast on highly-fluorescent prous surfaces will illuminated with UV radiation. The conjugated seven-membered ring of the tropolone adduct can be reacted further diazonium salts, which is demonstrated here with formation of two dyes. The methodology is extremely rapid, occurring in minutes with mild heating, and can be applied before ninhydrin in a chemical detection sequence. <br>


Tetrahedron ◽  
2016 ◽  
Vol 72 (22) ◽  
pp. 3124-3131 ◽  
Author(s):  
Tomohiro Umeno ◽  
Atsushi Ueda ◽  
Makoto Oba ◽  
Mitsunobu Doi ◽  
Takayuki Hirata ◽  
...  

ChemInform ◽  
2010 ◽  
Vol 31 (14) ◽  
pp. no-no
Author(s):  
Ouafaa El Mahdi ◽  
Jean-Pierre Lavergne ◽  
Jean Martinez ◽  
Philippe Viallefont ◽  
E. M. Essassi ◽  
...  

2014 ◽  
Vol 25 (10) ◽  
pp. 1761-1768 ◽  
Author(s):  
Takuma Kato ◽  
Makoto Oba ◽  
Koyo Nishida ◽  
Masakazu Tanaka

2020 ◽  
Author(s):  
Felix Reiners ◽  
Emanuel Joseph ◽  
Benedikt Nißl ◽  
Dorian Didier

Recent progress on four-membered ring building blocks has led us to investigate the formation of non-natural azetidine-based amino acids (<i>Aze</i>). A simple organometallic route was developed to access unsaturated carboxylic acids, which were further engaged in metal catalyzed asymmetric reduction. Functionalized <i>Aze</i> derivatives were finally employed in the formation of small peptide chains.


2019 ◽  
Vol 75 (8) ◽  
pp. 1182-1187 ◽  
Author(s):  
Akiko Asano ◽  
Mitsinobu Doi

The four azole rings place structural restrictions on ascidiacyclamide (ASC). As a result, the structure of ASC exists in an equilibrium between two major forms (i.e. folded and square). [D-βVal3,7]Ascidiacyclamide (βASC) was synthesized by replacing two D-Val-Thz (Val is valine and Thz is thiazole) blocks with D-β-Valine (D-βVal-Thz). This modification expands the peptide ring; the original 24-membered macrocycle of ASC becomes a 26-membered ring. Circular dichroism (CD) spectra showed that, in solution, the structural equilibrium is maintained with βASC, but the folded form is dominant. A copper complex was prepared, namely [[D-βVal3,7]ascidiacyclamide(2−)]aqua-μ-carbonato-dicopper(II) monohydrate, [Cu2(C38H54N8O6S2)(CO3)(H2O)]·H2O, to determine the effect of the change in ring size on the coordinated structure. The obtained bis-CuII–βASC complex contains two water molecules and a carbonate anion. Two CuII ions are chelated by three N-donor atoms of two Thz–Ile–Oxz (Ile is isoleucine and Oxz is oxazoline) units. An O atom of the carbonate anion bridges two CuII ions, forming two square pyramids. These features are similar to the previously reported structure of the CuII–ASC complex, but the two pyramids are enveloped inside the peptide and share one apex. In the CuII–ASC complex, the apex of each square pyramid is an O atom of a water molecule, and the two pyramids are oriented toward the outside of the peptide. The incorporated β-amino acids of βASC make the space inside the peptide large enough to envelop the two square pyramids. The observed structural changes in the bis-CuII–βASC complex arising from ring expansion are particularly interesting in the context of the previously reported structure of the CuII–ASC complex.


2019 ◽  
Author(s):  
Clara M. Agapie ◽  
Melissa Sampson ◽  
William Gee

The work describes a new chemical means of visualising latent fingerprints (fingermarks) using tropolone. Tropolone reacts with amino acids within the fingermark residue to form adducts that absorb UV radiation. These adducts provide useful contrast on highly-fluorescent prous surfaces will illuminated with UV radiation. The conjugated seven-membered ring of the tropolone adduct can be reacted further diazonium salts, which is demonstrated here with formation of two dyes. The methodology is extremely rapid, occurring in minutes with mild heating, and can be applied before ninhydrin in a chemical detection sequence. <br>


1976 ◽  
Vol 31 (2) ◽  
pp. 279-280 ◽  
Author(s):  
A. Kibfel ◽  
G. Will ◽  
R. Tschesche ◽  
H. Wilhelm

The constitution and conformation of the known cyclopeptide alkaloid mauritine-A were determined by X-ray diffraction methods. All amino acids belong to the L-series, 3-hydroxy proline has trans-configuration. As indicated by the UV-spectrum, the 14-membered ring system is considerably strained.


2014 ◽  
Vol 12 (17) ◽  
pp. 2641 ◽  
Author(s):  
Woohyung Lee ◽  
Sunmi Kwon ◽  
Philjae Kang ◽  
Ilia A. Guzei ◽  
Soo Hyuk Choi

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