Skip to main content
Log in

Carbohydrate recognition of symmetrical tripodal receptor type tris(2-aminoethyl)amine derivatives

  • Published:
Journal of Thermal Analysis and Calorimetry Aims and scope Submit manuscript


Carbohydrate recognition of some bioactive symmetrical tripodal receptor type tris(2-aminoethyl)amine (TAEA) derivatives was investigated. In calorimetric experiments, the highest binding constant (Ka) of compound C (C35H49N5O4S) with methyl α-d-mannopyranoside was Ka = 858 M−1 with 1:1 stoichiometry. Formation of hydrogen bonds in binding between symmetrical tripodal receptor type compound C and sugars was suggested by the large negative values of ∆H° (=−34 to −511 kJ mol−1). In a comparison of each set of α- and β-anomers of some monosaccharides (methyl α/β-d-galactopyranoside, methyl α/β-d-glucopyranoside, and methyl α/β-l-fucopyranoside), compound C showed that the binding constant of β-anomer was larger than that of the corresponding α-anomer, indicating higher β-anomer selectivity. The calculated energy-minimized structure of the complex of compound C with guest methyl α-d-mannopyranoside is also presented. The experimental results obtained from this work indicated that symmetrical tripodal receptor type TAEA derivative C has a lectin-like carbohydrate recognition property.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Subscribe and save

Springer+ Basic
EUR 32.99 /Month
  • Get 10 units per month
  • Download Article/Chapter or Ebook
  • 1 Unit = 1 Article or 1 Chapter
  • Cancel anytime
Subscribe now

Buy Now

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1
Fig. 2
Fig. 3

Similar content being viewed by others


  1. Oshovsky GV, Reinhoudt DN, Verboom W. Supramolecular chemistry in water. Angew Chem Int Ed. 2007;46:2366–93.

    Article  CAS  Google Scholar 

  2. Mibu N, Yokomizo K, Uchida W, Takemura S, Zhou J, Aki H, Miyata T, Sumoto K. Molecular symmetry and biological activities of new symmetrical tris(2-aminoethyl)amine derivatives. Chem Pharm Bull. 2012;60:408–14.

    Article  CAS  Google Scholar 

  3. Mazik M, Sonnenberg C. Isopropylamino and isobutylamino groups as recognition sites for carbohydrates: acyclic receptors with enhanced binding affinity toward β-galactosides. J Org Chem. 2010;75:6416–23.

    Article  CAS  Google Scholar 

  4. Humblet V, Misra P, Bhushan KR, Nasr K, Ko Y-S, Tsukamoto T, Pannier N, Frangioni JV, Maison W. Multivalent scaffolds for affinity maturation of small molecule cell surface binders and their application to prostate tumor targeting. J Med Chem. 2009;52:544–50.

    Article  CAS  Google Scholar 

  5. Kim J, Kim S-G, Seong HR, Ahn KH. Breaking the C 3-symmetry of chiral tripodal oxazolines: enantio-discrimination of chiral organoammonium ions. J Org Chem. 2005;70:7227–31.

    Article  CAS  Google Scholar 

  6. Mibu N, Yokomizo K, Oishi M, Miyata T, Sumoto K. Synthesis and antiviral activities of N-mono- and/or N,N′-di-carbamoyl and acyl derivatives of symmetrical diamines. Chem Pharm Bull. 2008;56:1052–8.

    Article  CAS  Google Scholar 

  7. Mibu N, Yokomizo K, Saisho M, Oishi M, Aki H, Miyata T, Sumoto K. Synthesis and biological activities of some N-acyl-2,6-diaminopyridines and related linker mode identical twin drugs. Heterocycles. 2011;83:385–93.

    Article  CAS  Google Scholar 

  8. Mibu N, Yokomizo K, Miyata T, Sumoto K. Synthesis and antiviral activities of some heteroaryl-substituted triarylmethanes. J Heterocycl Chem. 2010;47:1434–8.

    Article  CAS  Google Scholar 

  9. Fujisaki F, Usami H, Nakashima S, Iwashita S, Kurose Y, Kashige N, Miake F, Sumoto K. Synthesis of the identical linker mode twin-drug type C 2-symmetrical molecules. Heterocycles. 2011;83:1843–51.

    Article  CAS  Google Scholar 

  10. Tobey SL, Anslyn EV. Studies into the thermodynamic origin of negative cooperativity in ion-pairing molecular recognition. J Am Chem Soc. 2003;125:10963–70.

    Article  CAS  Google Scholar 

Download references


We thank Mr. Masato Ishimaru for his valuable technical assistance.

Author information

Authors and Affiliations


Corresponding author

Correspondence to Kunihiro Sumoto.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Mibu, N., Aki, H., Ikeda, H. et al. Carbohydrate recognition of symmetrical tripodal receptor type tris(2-aminoethyl)amine derivatives. J Therm Anal Calorim 113, 1015–1018 (2013).

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: