Next Article in Journal
2,4-Bis[(2,6-diisopropylphenyl)imino]-3-methylpentan-3-ol
Previous Article in Journal
Octahydro-1H,5H,7H-dipyrrolo[1,2-c:1′,2′-f][1,3,6]oxadiazocine-5-thione
Article Menu

Export Article

Open AccessShort Note
Molbank 2018, 2018(2), M994; https://doi.org/10.3390/M994

N-(1-Deoxy-α-d-tagatopyranos-1-yl)-N-methylaniline (“d-Tagatose-N-methylaniline”)

1
Department of Biochemistry, University of Missouri, Columbia, MO 65211, USA
2
Department of Chemistry, University of Missouri, Columbia, MO 65211, USA
*
Author to whom correspondence should be addressed.
Received: 17 April 2018 / Revised: 6 May 2018 / Accepted: 7 May 2018 / Published: 9 May 2018
(This article belongs to the Section Structure Determination)
Full-Text   |   PDF [5006 KB, uploaded 9 May 2018]   |  

Abstract

Tagatosamines form in thermally-processed dairy products and contribute to the foods’ organoleptic and nutritional value. d-Tagatose-N-methylaniline (N-(1-deoxy-d-tagatos-1-yl)-N-methylaniline, 1-deoxy-1-(N-methylphenylamino)-d-tagatose) was synthesized from d-galactose via the Amadori rearrangement. In aqueous solution, it established an anomeric equilibrium consisting of 62.8% α-pyranose, 21.3% β-pyranose, 1.5% α-furanose, 8.1% β-furanose, and 6.2% acyclic keto tautomer. The crystalline α-pyranose anomer of d-tagatose-N-methylaniline adopted the 5C2 chair conformation. All hydroxyl and ring oxygen atoms and the amino nitrogen are involved in an extensive H-bonding network dominated by infinite homodromic chains. The Hirshfeld surface analysis suggests a significant contribution of non-polar intermolecular contacts to the crystal structure. View Full-Text
Keywords: carbohydrate; amino sugar; 1-deoxy-1-(N-methylphenylamino)-d-tagatose; tagatosamine; Amadori compound; tautomerization; crystal structure; Hirshfeld surface carbohydrate; amino sugar; 1-deoxy-1-(N-methylphenylamino)-d-tagatose; tagatosamine; Amadori compound; tautomerization; crystal structure; Hirshfeld surface
Figures

Graphical abstract

This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

Supplementary materials

SciFeed

Share & Cite This Article

MDPI and ACS Style

Mossine, V.V.; Barnes, C.L.; Mawhinney, T.P. N-(1-Deoxy-α-d-tagatopyranos-1-yl)-N-methylaniline (“d-Tagatose-N-methylaniline”). Molbank 2018, 2018, M994.

Show more citation formats Show less citations formats

Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]
Molbank EISSN 1422-8599 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top