86731-89-7Relevant articles and documents
Structure-property relationship study of n-(hydroxy)peptides for the design of self-assembled parallel β-sheets
Roche, Stéphane P.,Richaud, Alexis D.
, p. 12329 - 12342 (2020/11/10)
The design of novel and functional biomimetic foldamers remains a major challenge in creating mimics of native protein structures. Herein, we report the stabilization of a remarkably short β-sheet by incorporating N-(hydroxy)glycine (Hyg) residues into the backbone of peptides. These peptide- peptoid hybrids form unique parallel β-sheet structures by selfassembly upon hydrogenation. Our spectroscopic and crystallographic data suggest that the local conformational perturbations induced by N-(hydroxy)amides are outweighed by a network of strong interstrand hydrogen bonds.
Process for preparing 1-substituted pyrrole-3-carboxylic acid derivatives
-
, (2008/06/13)
A simple and industrially viable process for preparing a 1-substituted pyrrole-3-carboxylic acid derivative of formula (I) is provided. The process comprises reacting a compound of formula (II), a compound of formula (III), and an acid anhydride according
Experiments towards the Synthesis of the Ergot Alkaloids and Related Structures. Part 6. N-Acyl-N-(1,2,3,4-tetrahydro-1-oxo-2-naphthyl)glycines and a New Aromatisation Reaction
Bowman, Ralph E.
, p. 897 - 901 (2007/10/02)
Three methods are reported for the preparation of N-(1,2,3,4-tetrahydro-1-oxo-2-naphthyl)glycine (4; R=H) hydrochloride from which the title compounds may be prepared.In the first, hydrolysis of the oxazolinone ester (3; R=CH2CO2Me, n=1) with concentrated hydrochloric acid in acetic acid furnished a mixture (ca. 4:1) of the hydrochlorides of the required amino-keto-acid (4; R=H) and β-naphthylglycine (5; R1=R2=H) which were easily separable.In the second, a similar hydrolysis of the homologous oxazinedione (3; R=CH2CO2Me, n=2) furnished it as the sole product in quantitative yield.In the third, 2-aminotetralone hydrochloride (7) was treated in formic acid solution with glyoxylic acid (ca. 3 mol equiv.) in the presence of base to give the N-formyl-keto-acid (10=4; R=CHO) in a crude yield of 85percent and from which the hydrochloride of (4; R=H) was obtained by hydrolysis.Benzylamine reacted similarly to give N-formyl-N-benzylglycine but secondary amines do not appear to undergo this novel condensation-reduction reaction.Uncatalysed formolysis of the oxazolinone ester (3; R=CH2CO2Me, n=1) furnished, in essentially quantitative yield, methyl N-formyl-2-naphthylglycinate (5; R1=CHO, R2=Me) - a new aromatisation reaction which may well be of general utility since the parent oxazolinone and its N-methyl derivative behaved similarly.