The diastereomers of mannosylerythritol lipids have different interfacial properties and aqueous phase behavior, reflecting the erythritol configuration

Carbohydrate Research
Tokuma FukuokaDai Kitamoto

Abstract

Mannosylerythritol lipids (MELs) produced by yeasts are one of the most promising glycolipid biosurfactants. There are two MEL diastereomers, in which the configurations of the erythritol moieties are opposite. The 4-O-β-D-mannopyranosyl-(2S,3R)-erythritol (S-form) or 4-O-β-D-mannopyranosyl-(2R,3S)-erythritol (R-form) is the hydrophilic domain. In this study, we prepared S- and R-form MEL homologs with similar fatty acyl groups, and compared their interfacial properties. Among the four diastereomers (S-MEL-B and -D/R-MEL-B and -D), R-form MELs showed a higher critical aggregation concentration and hydrophilicity compared to the corresponding S-form. R-form MELs also efficiently formed relatively large vesicles compared to S-form. Moreover, we estimated the binary phase diagram of the MEL-water system and compared the aqueous phase behavior among the four diastereomers. The present MELs self-assembled into a lamellar (L(α)) structure at all concentration ranges. Meanwhile, the one-phase L(α) region of R-form MELs was wider than those of S-form MELs. R-form MELs may maintain more water between the polar layers in accordance with an extension of the interlayer spacing. These results suggest that the differences in MEL carbohydrate...Continue Reading

References

Apr 21, 2006·Journal of Controlled Release : Official Journal of the Controlled Release Society·Saki IgarashiYoshie Maitani
Feb 7, 2007·Langmuir : the ACS Journal of Surfaces and Colloids·Tomohiro ImuraDai Kitamoto
Sep 22, 2007·Journal of Controlled Release : Official Journal of the Controlled Release Society·Yoshinobu UenoMamoru Nakanishi
May 6, 2008·Colloids and Surfaces. B, Biointerfaces·Wannasiri WorakitkanchanakulDai Kitamoto
Dec 17, 2008·Colloids and Surfaces. B, Biointerfaces·Wannasiri WorakitkanchanakulDai Kitamoto
May 1, 2010·Journal of Oleo Science·Tomotake MoritaDai Kitamoto
Jul 14, 2010·Journal of Oleo Science·Tomotake MoritaDai Kitamoto

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Citations

Apr 16, 2013·Applied Microbiology and Biotechnology·Tomotake MoritaDai Kitamoto
Apr 26, 2012·Journal of Oleo Science·Tokuma FukuokaDai Kitamoto
Feb 18, 2014·Applied Microbiology and Biotechnology·Sophie L K W RoelantsWim Soetaert
Apr 22, 2015·Journal of Oleo Science·Tokuma FukuokaHiroko Kitamoto
May 11, 2015·Applied Microbiology and Biotechnology·Tomotake MoritaDai Kitamoto
Jun 22, 2018·Applied Microbiology and Biotechnology·Azusa SaikaTomotake Morita
Jan 26, 2020·Applied Microbiology and Biotechnology·Ana Letícia Silva CoelhoDébora de Oliveira
Nov 17, 2021·Chembiochem : a European Journal of Chemical Biology·Takanori KondoKazunobu Toshima

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