Phthaloyl-L-alanine
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Phthaloyl-L-alanine

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Category
Cyclic Amino Acids
Catalog number
BAT-003454
CAS number
4192-28-3
Molecular Formula
C11H9NO4
Molecular Weight
219.20
Phthaloyl-L-alanine
Synonyms
Pht-L-Ala-OH; (S)-2-(1,3-Dioxoisoindolin-2-yl)propanoic acid
Appearance
White solid
Purity
≥ 98% (HPLC)
Density
1.467±0.06 g/cm3(Predicted)
Melting Point
143.1-145.2 °C
Boiling Point
407.9±28.0 °C(Predicted)
Storage
Store at 2-8 °C
InChI
InChI=1S/C11H9NO4/c1-6(11(15)16)12-9(13)7-4-2-3-5-8(7)10(12)14/h2-6H,1H3,(H,15,16)/t6-/m0/s1
InChI Key
OZWUITKBAWTEAQ-LURJTMIESA-N
Canonical SMILES
CC(C(=O)O)N1C(=O)C2=CC=CC=C2C1=O
1. Recognition of guests by water-stabilized cavitand hosts
Agustí Lledó, Richard J Hooley, Julius Rebek Jr Org Lett. 2008 Sep 4;10(17):3669-71. doi: 10.1021/ol801228b. Epub 2008 Jul 26.
Water stabilized, deep cavitands with three walls and an open side are shown to be receptors for amines and ammonium cations bearing bulky aliphatic groups. The missing wall allows the binding of guests not accommodated by the four-walled counterparts.
2. An extended cavitand with an introverted carboxylic acid
Shengxiong Xiao, Dariush Ajami, Julius Rebek Jr Chem Commun (Camb). 2010 Apr 14;46(14):2459-61. doi: 10.1039/b926072b. Epub 2010 Feb 25.
The condensation of a Kemp's triacid derivative with a diamino resorcinarene yielded a cavitand with the deepest cavity prepared to date featuring an inwardly-directed carboxylic acid. The extended 6,7-diaminoquinoxaline wall bearing the acid allowed accommodation of large amines, such as 1-adamantanemethylamine, as well as smaller amines such as triethylamine. Adamantyl and cyclohexyl isocyanides are also bound in the deep cavitand in a way that positions the isonitrile function near the carboxylic acid group. Reaction occurs inside the cavity at ambient temperature to form the respective N-acylformamides. Low concentrations of the transient O-acyl isoamide intermediate were detected by (1)H NMR and IR spectroscopy.
3. Synthesis, structure, and binding properties of lipophilic cavitands based on a calix[4]pyrrole-resorcinarene hybrid scaffold
Albano Galán, Eduardo C Escudero-Adán, Antonio Frontera, Pablo Ballester J Org Chem. 2014 Jun 20;79(12):5545-57. doi: 10.1021/jo5007224. Epub 2014 May 30.
We report the synthesis, structural characterization, and binding properties of a series of unprecedented cavitands based on a meso-dodecyl-calix[4]pyrrole-resorcin[4]arene hybrid scaffold. The reported structural and conformational features of the prepared cavitands are derived from results obtained in solution, solid state, and molecular modeling studies. In the solid state, these cavitands are exclusively observed in the kite C4 structure and as a racemic mixture of two cyclochiral conformers, which are interconverting fast on the (1)H NMR time scale, according to solution studies. In agreement, molecular modeling studies assign an energy preference for the kite conformer of the cavitands. The polar interior of the synthesized containers allows for the inclusion of a series of pyridine N-oxide derivatives. This results in the formation of 1:1 complexes that are kinetically and thermodynamically highly stable. The putative switching process between the vase and kite forms of these cavitands is investigated in solution by means of variable temperature (1)H NMR experiments. N-Oxide guests that are size and shape complementary to the volume of the cavity of the vase form are also employed to facilitate its emergence. All of the results obtained indicate the existence of a remarkable preference toward the kite conformation both in free and bound calix[4]pyrrole-based cavitands.
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