Fluorescence Studies with Tryptophan Analogs: Excited State Interactions Involving the Side Chain Amino Group

1995 ◽  
Vol 99 (15) ◽  
pp. 5713-5723 ◽  
Author(s):  
Maurice R. Eftink ◽  
Jiwei Jia ◽  
Dana Hu ◽  
Camillo A. Ghiron
1988 ◽  
Vol 53 (11) ◽  
pp. 2810-2824 ◽  
Author(s):  
Ilmars Sekacis ◽  
Mark Shenderovich ◽  
Gregory Nikiforovich ◽  
Edvards Liepinš ◽  
Ludmila Polevaya ◽  
...  

A group of synthetic peptides including Boc-Lys-Phe-X-Y, X = Ala (I, III) or Thr (II), Y = Pro (I, II) or Ala (III) was studied by means of 1H NMR spectroscopy and theoretical conformational analysis. Compound I in DMSO shows two conformers with the trans- and cis-configuration of the peptide bond Ala-Pro. The salt bridge between the Lys ε-amino group and the C-terminal carboxyl is featured by magnetic nonequivalence of the Lys CεH2 protons. The space structure of I and II was found to possess a salt bridge fixed by an unusual turn in the chain formed by the Lys side chain and the C-terminal dipeptide with the trans-peptide bond X-Pro. Since a stable ionic bond in III and in the cis-conformer of I has not been observed, its contribution to stabilization of the space structure of the peptides in DMSO appears rather small.


ChemSusChem ◽  
2016 ◽  
Vol 9 (13) ◽  
pp. 1623-1633 ◽  
Author(s):  
Ning-Jiu Zhao ◽  
Mao-Jie Zhang ◽  
Ran Liang ◽  
Li-Min Fu ◽  
Wei Zhang ◽  
...  
Keyword(s):  

2012 ◽  
Vol 132 (11) ◽  
pp. 2997-3003 ◽  
Author(s):  
Xiaoquan Zhou ◽  
Geoffrey B. Piland ◽  
Dharmalingam Kurunthu ◽  
Robert J. Dillon ◽  
Jonathan J. Burdett ◽  
...  

1996 ◽  
Vol 51 (11-12) ◽  
pp. 772-780 ◽  
Author(s):  
R Michalke ◽  
K Taraz ◽  
H Budzikiewiez

For azoverdin, the siderophore of Azomonas macrocytogenes ATCC 12334, a pyoverdintype structure has been suggested. We now present evidence that it is actually an isopyoverdin. Also the sequence of the peptide chain has to be revised. Azoverdin comprises, therefore, the chromophore (3S)-5-amino-1,2-dihydro-8,9-dihydroxy-3H -pyrimido[1,2a]quinoline- 3-carboxylic acid whose amino group is bound to a succinamide residue while the carboxyl group is attached to the N -terminus of L-Hse-[2-(R-1-amino-3-hydroxypropyl)-3,4,5,6- tetrahydropyrimidine-65-carboxylic acid]-N5-acetyl-N5,-hydroxy-ᴅ-Orn-ᴅ-Ser-N5-acetyl-N5- hydroxy-ʟ-Orn. In addition to azoverdin congeners with succinic acid (azoverdin A ) and with ʟ-Glu (azoverdin G ), resp., instead of the succinamide side chain could be isolated.


2010 ◽  
Vol 2010 ◽  
pp. 1-6 ◽  
Author(s):  
Jakob Kljun ◽  
Saša Petriček ◽  
Dušan Žigon ◽  
Rosana Hudej ◽  
Damijan Miklavčič ◽  
...  

Novel ruthenium(III) complexes with histamine[RuCl4(dmso-S)(histamineH)]⋅O(1a) and[RuCl4(dmso-S)(histamineH)](1b) have been prepared and characterized by X-ray structure analysis. Their crystal structures are similar and show a protonated amino group on the side chain of the ligand which is not very common for a simple heterocyclic derivative such as histamine. Biological assays to test the cytotoxicity of the compound1bcombined with electroporation were performed to determine its potential for future medical applications in cancer treatment.


1971 ◽  
Vol 49 (19) ◽  
pp. 3143-3151 ◽  
Author(s):  
K. Bailey ◽  
A. W. By ◽  
K. C. Graham ◽  
D. Verner

Data from the p.m.r. spectra of β-amino-, β-aminohydrochloride-, β-hydroxy-, and β-nitro-α-phenyl-propanes having methyl or methoxy substituants on the phenyl ring (37 compounds in all) are presented. The α and β protons of the side-chain give a pattern usually analyzable as ABX. The data are discussed in terms of correlations of coupling constants and chemical shifts with electronegativity of the substituent groups, steric and electronic effects, and apparent changes in rotamer populations. Hydrogen-bonding between the amino group of amphetamines and a methoxyl function at the ortho position in the phenyl ring is indicated for the salts but not the free bases.


Pteridines ◽  
1999 ◽  
Vol 10 (3) ◽  
pp. 79-90 ◽  
Author(s):  
Hermann Traub ◽  
Wolfgang Pfleiderer

Summary A series of new 6-substituted 2,4-diaminopteridines (3-23) and pterins (26-43) have been synthesized by nucleophilic displacement reactions at the side chain of 6-bromomethyl-2,4-diaminopteridine (2) and 6- bromomethylpterin (25) using various types of 0-, N- and S-nucleophiles. Acid and base hydrolyses allow easy conversion of the 2,4-diaminopteridines (3-5, 7, 9, 10, 12, 19-21 and 23) into the corresponding pterins (26-32, 39-42). Acylations take place at the amino as well as at the functional groups in the side chain (44-46). A versatile protection of the amino group in pterins is its transformation into the N ,N -dimethylaminomethylcnimino function by amide-acetals (47, 50) allowing subsequently selective acylations at the side chain (48, 49).


2007 ◽  
Vol 126 (2) ◽  
pp. 728-734 ◽  
Author(s):  
Fabiano Severo Rodembusch ◽  
Fernando Paulus Leusin ◽  
Leandra Franciscato Campo ◽  
Valter Stefani

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