Skip to content
Licensed Unlicensed Requires Authentication Published by De Gruyter June 18, 2020

Synthesis, Characteristics and Application of Novel Non-Ionic Gemini Surfactants as Reverse Micellar Systems for Encapsulation of Some Aromatic α-Amino Acids in n-Hexane

Synthese, Eigenschaften und Anwendung neuartiger nichtionischer Gemini-Tenside als reverse Mizellensysteme zur Verkapselung einiger aromatischer α-Aminosäuren in n-Hexan
  • Nirmal Singh and Lalit Sharma


Non-ionic carbohydrate based gemini surfactants with rigid aromatic spacer CH2-Ar-CH2, which carry two hydrophobic tails of different tail lengths (C12, C14 and C16) and two sugar moiety polar head groups were synthesized and their reverse micellar behavior for solubilization of some aromatic α-amino acids viz. histidine (His), phenylalanine (Phy), tyrosine (Tyr) and tryptophan (Trp) in n-hexane were studied by spectroscopic analysis. The head group of these gemini surfactants consists of sugar moiety connected to C-6 of tertiary amines. Amino acids form complexes in order of His > Phy > Tyr > Trp, and in all cases it was found that the D-enantiomers solubilize better in comparison to the L-enantiomers. Moreover, more hydrophobic surfactants i.-e. surfactants with longer hydrocarbon tails show greater complex formation tendency towards D- and L-enantiomers of aromatic α-amino acids.


Nichtionische Gemini-Tenside auf Kohlenhydratbasis mit starrem aromatischem Spacer CH2-Ar-CH2, die zwei unterschiedlich lange hydrophobe Schwänze (C12, C14 und C16) und zwei polare Kopfgruppen der Zuckereinheit tragen, wurden synthetisiert. Ihr umgekehrtes mizellares Verhalten zur Solubilisierung einiger aromatischer α-Aminosäuren, nämlich Histidin (His), Phenylalanin (Phy), Tyrosin (Tyr) und Tryptophan (Trp) in n-Hexan wurde durch spektroskopischen Methoden analysiert. Die Hauptgruppe dieser Geminitenside besteht aus einer Zuckereinheit, die an C-6 der tertiären Amine gebunden ist. Die Aminosäuren bilden Komplexe in der Reihenfolge von His > Phy > Tyr > Trp, und es wurde in allen Fällen festgestellt, dass die D-Enantiomere im Vergleich zu den L-Enantiomeren besser solubilisieren. Darüber hinaus zeigen hydrophobere Tenside, d.-h. Tenside mit längeren Kohlenwasserstoffschwänzen, eine größere Tendenz zur Komplexbildung gegenüber den D- und L-Enantiomeren von aromatischen α-Aminosäuren.

Correspondence address, Mr. Nirmal Singh, Post Graduate Department of Chemistry, RSD College, Ferozepur City–152002 (Pb.), India, E-Mail: , Tel.: +919501562900
Correspondence address, Dr. Lalit Sharma, Department of Applied Sciences & Humanities Shaheed Bhagat Singh State Technical Campus Ferozepur–152004 (Pb.), India, E-Mail:


1 C. A. Bunton , L. B.Robinson, J.Schaak and M. F.Stam: J. Org. Chem.36 (1971): 2346. 10.1021/jo00815a033Search in Google Scholar

2 R. Zana and Y.Talmon: Nature. 362 (1993): 228. 10.1038/362228a0Search in Google Scholar

3 F. M. Menger and C. A.Littau: J. Am. Chem. Soc.115 (1993) 10083. 10.1021/ja00062a086Search in Google Scholar

4 R. Zana : (1996) Specialist surfactants in: I. D.Robb (ed.) p. 81. Champman Hall Ltd., London. 10.1007/978-94-009-1557-2_4Search in Google Scholar

5 F. M. Menger and B. N. A.Mbadugha: J. Am. Chem. Soc. 123 (2001) 875. 11456621 10.1021/ja0033178Search in Google Scholar PubMed

6 M. L. Fielden , C.Perrin, A.Kremer, M.Bergsma, M. C.Stuart, P.Camilleri and J. B. F. N.Engberts: Eur. J. Biochem. 268 (2001) 1269. 11231278 10.1046/j.1432-1327.2001.01995.xSearch in Google Scholar PubMed

7 A. Wagenaar and J. B. F. N.Engberts: Tetrahedron63 (2007) 10622. 10.1016/j.tet.2007.08.023Search in Google Scholar

8 S. Warwel F. Bruse and H.Schier: J. Surfact Deterg. 7 (2004) 181. 10.1007/s11743-004-0302-1Search in Google Scholar

9 S. Warwel and F.Bruse: J. Surfact Deterg. 7 (2004) 187. 10.1007/s11743-004-0303-0Search in Google Scholar

10 Y. Takamatsu K. Torigue T. Yoshimura K. Esumi H. Sakai and M.Abe: Colloids Surfaces A328 (2008) 100. 10.1016/j.colsurfa.2008.06.033Search in Google Scholar

11 K. A. Wilk U. Laska K. Zielinski and A.Olszowski: J. Photochem Photobiol A Chem. 219 (2011) 204. 10.1016/j.jphotochem.2011.02.011Search in Google Scholar

12 M. Pisarcik , M.Polakovicova, M.Markuliak, M.Lukac and F.Devinsky: Molecules, 24 (2019) 1481. 31801214 10.3390/molecules24081481Search in Google Scholar PubMed PubMed Central

13 N. Singh and L.Sharma: Lett Org Chem., 16 (2019) 607. 10.2174/1570178616666181210103350Search in Google Scholar

14 Y. Cheng , Y.Yang, C.Niu, Z.Feng, W.Zhao and S.Lu: Frontiers Materials Sci., 13 (2019), 242. 10.1007/s11706-019-0473-0Search in Google Scholar

15 N. Singh and L.Sharma: Tenside Surfact Det. 55 (2018) 220. 10.3139/113.110561Search in Google Scholar

16 N. Fatma , M.Panda and K.Din: Tenside Surfact Det., 55 (2018) 210. 10.3139/113.110559Search in Google Scholar

17 J. H. Lee , J.Ahn, M.Masuda, J.Jaworski and J. H.Jung: Langmuir, 29 (2013) 13535. 10.1021/la402519zSearch in Google Scholar PubMed

18 V. Neto , R.Granet and P.Krausz: Tetrahedron, 66 (2010) 4633. 10.1016/j.tet.2010.03.115Search in Google Scholar

19 M. J. L. Castro , A. F.Cirelli and J.Kovensky: J. Surfactants Deterg. 9 (2006) 279. 10.1007/s11743-006-5008-xSearch in Google Scholar

20 L. Sharma , Saroj and Singh, N.: Tenside Surf. Deterg. 51 (2014) 441. 10.3139/113.110327Search in Google Scholar

21 L. Sharma , Saroj and Singh, N.: J. Surfact Deterg. 18 (2015) 33. 10.1007/s11743-014-1595-0Search in Google Scholar

22 L. Sharma and Saroj: J. Incl. Phenom Macrocycl Chem. 74 (2012) 251. 10.1007/s10847-012-0107-ySearch in Google Scholar

23 P. Patial A. Shaheen and I.Ahmed: J. Surfact Deterg. 17 (2014) 253. 10.1007/s11743-013-1472-2Search in Google Scholar

24 H. Ohle and L. V.Vargha: Berichte62 (1929) 2435. 10.1002/cber.19290620883Search in Google Scholar

25 L. D. Hall , S. A.Black, K. N.Seessor and A. S.Tracey: Can. J. Chem. 50 (1972) 1912. 10.1139/v72-307Search in Google Scholar

26 D. M. Vyas , H. C.Jarrell and W. A.Szarek: Can. J. Chem. 53 (1975) 2748. 10.1139/v75-188Search in Google Scholar

27 W. C. Griffin : Calculation of HLB values of non-ionic surfactants. J. Soc. Cosmet. Chem. 5 (1954) 249.Search in Google Scholar

Received: 2019-12-10
Accepted: 2020-02-26
Published Online: 2020-06-18
Published in Print: 2020-05-15

© 2020, Carl Hanser Publisher, Munich

Downloaded on 6.12.2023 from
Scroll to top button