Pergamon Tetrahedron: Asymmetry 9 (1998) 2113–2119 TETRAHEDRON: ASYMMETRY Bioactive glycoglycerolipid analogues: an expeditious enzymatic approach to mono- and diesters of 2-O-β- D-galactosylglycerol Diego Colombo, a Fiamma Ronchetti, a,∗ Antonio Scala a and Lucio Toma b a Dipartimento di Chimica e Biochimica Medica, Università di Milano, Via Saldini 50, 20133 Milano, Italy b Dipartimento di Chimica Organica, Università di Pavia, Via Taramelli 10, 27100 Pavia, Italy Received 21 April 1998; accepted 19 May 1998 Abstract 2-O-β-D-Galactosylglycerol 1 was submitted to acylation using Pseudomonas cepacia or Candida antarctica lipases as catalysts and 2,2,2-trifluoroethyl esters of butanoic, hexanoic, octanoic or decanoic acid as acyl carriers. Taking advantage of the high diastereoselectivity and regioselectivity of the two enzymes, the 1-O-, 3-O-, 6 ′ -O- acyl and the 1,6 ′ -di-O-acylderivatives of 1 were obtained pure or in an appreciably enriched form. © 1998 Elsevier Science Ltd. All rights reserved. 1. Introduction Glycoglycerolipids from natural sources exhibit several interesting activities; in particular, some of them have recently shown both in vitro and in vivo tumour inhibitory activity. 1–3 In this context, in order to ascertain the structural features responsible for the activity, we have performed several syntheses of bioactive gluco- and galactosylglycerols through chemoenzymatic approaches; 4–6 we found that non- natural analogues of the glucose series bearing medium length fatty acid acyl chains, shorter than the chains present in the natural compounds, exhibited a more pronounced activity. 3 Moreover, the nature of the carbohydrate moiety of glycosylglycerols also has an influence on the cancer chemoprevention activity; in particular the presence of galactose makes, in some cases, 1 the compounds more active than the presence of glucose; thus, we have turned our efforts to the preparation of mono- and diesters of 2-O-β-D-galactosylglycerol 1 with medium length fatty acid acyl chains. ∗ Corresponding author. Tel: +39-2-70645222; fax +39-02-2361407; e-mail: fiamma.ronchetti@unimi.it 0957-4166/98/$19.00 © 1998 Elsevier Science Ltd. All rights reserved. PII: S0957-4166(98)00207-9