5-Amino-1-naphthol

5-Amino-1-naphthol, a novel 1,5-naphthalene derivative matrix suitable for matrix-assisted laser desorption/ionization in-source decay of phosphorylated peptides.[Pubmed:23239322]

Rapid Commun Mass Spectrom. 2013 Jan 15;27(1):103-8.

RATIONALE: Although matrix-assisted laser desorption/ionization in-source decay (MALDI-ISD) is an important method for post-translational modification (PTM) analysis, the conventional matrices, 2,5-dihydroxybenzoic acid (2,5-DHB) and 1,5-diaminonaphthalene (1,5-DAN), are poor in terms of the fragment ion yields of the phosphorylated peptides. The use of 5-Amino-1-naphthol (5,1-ANL) as a novel matrix for ISD of phosphorylated peptides in MALDI time-of-flight mass spectrometry (TOFMS) is described here. METHODS: We have evaluated the ion yields of ISD fragments obtained from phosphorylated peptides using three 1,5-naphthalene derivatives as MALDI-ISD matrices, i.e., 5,1-ANL, 1,5-DAN and 1,5-dihydroxynaphthalene (1,5-DHN). The signal-to-noise ratio (S/N) of c'-series ions obtained from these matrices was used to estimate their suitability for MALDI-ISD of non-modified and phosphorylated peptides. RESULTS: The order of the S/N values of the ISD fragments for non-modified and phosphorylated peptides were 1,5-DAN > 5,1-ANL > 1,5-DHN and 5,1-ANL > 1,5-DHN > 1,5-DAN, respectively. CONCLUSIONS: The newly introduced matrix 5,1-ANL gave highest ion yields of ISD fragments from mono-, di-, and tetraphosphorylated peptides, while 1,5-DAN was poor in the ISD ion yields for phosphorylated peptides.

5-Amino-1-naphthol: two-dimensional sheets built up from R(4)(4)(18) rings formed by O-H...N, N-H...O and pi-pi interactions.[Pubmed:19893237]

Acta Crystallogr C. 2009 Nov;65(Pt 11):o565-8.

The crystal structure of the title compound, C(10)H(9)NO, (I), contains intermolecular O-H...N and N-H...O hydrogen bonds which together form sheets parallel to the (001) plane containing rings with an unusual R(4)(4)(18) motif. These rings are additionally stabilized by an intermolecular pi-pi stacking interaction. The significance of this study lies in the comparison drawn between the molecular structure of (I) and those of related compounds (1,5-diaminonaphthalene, 8-amino-2-naphthol, 3-amino-2-naphthol and aniline), which shows a close similarity in the noncoplanar orientation of the amine group and the aromatic moiety. Comparison of the crystal structures of (I) and several of its simple analogues (1-naphthol, naphthalene-1,4-diol, naphthalene-1,5-diol and 4-chloro-1-naphthol) shows a close similarity in the packing of the molecules, which form pi-stacks along the shortest crystallographic axes with a substantial spatial overlap between adjacent molecules.

5-Amino-1-naphthol.[Pubmed:21578535]

Acta Crystallogr Sect E Struct Rep Online. 2009 Oct 31;65(Pt 11):o2964.

In the title compound, C(10)H(9)NO, the amino and the hydr-oxy groups act both as a single donor and a single acceptor in hydrogen bonding. In the crystal, mol-ecules are connected via chains of inter-molecular cdots, three dots, centeredN-Hcdots, three dots, centeredO-Hcdots, three dots, centered inter-actions, forming a two-dimensional polymeric structure resembling the hydrogen-bonded mol-ecular assembly found in the crystal structure of naphthalene-1,5-diol. Within this layer, mol-ecules related by a translation along the a axis are arranged into slipped stacks via pi-pi stacking inter-actions [inter-planar distance = 3.450 (4) A]. The amino N atom shows sp(3) hybridization and the two attached H atoms are located on the same side of the aromatic ring.