Enzymatic production of sphingophospholipid derivatives

Claim 1

A process for producing a sphingophospholipid derivative reprsented by the following formula (I) ##STR10## wherein A and R' are as defined below, which comprises reacting a sphingophospholipid represented by the following formula (II) ##STR11## wherein A is a moiety represented by the following formula (i) ##STR12## or the following formula (ii) ##STR13## in which R represents a saturated or unsaturated aliphatic hydrocarbon group having 16 to 24 carbon atoms, and B represents --(CH 2 ) 2 N + (CH 3 ) 3 , --(CH 2 ) 2 NH 2 or --CH 2 CH(OH)CH 2 (OH), with a compound having an alcoholic hydroxyl group selected from the group consisting of (1) alcohol compounds having a primary alcoholic hydroxyl group and a C 1 -C 20 saturated or unsaturated aliphatic or aromatic hydrocarbon group R' which may be substituted by a substituent selected from the group consisting of halogen, amino, carboxyl and hydroxyl; alcohol compounds having a primary alcoholic hydroxyl group and a residue R' of a C 1 -C 20 saturated or unsaturated aliphatic or aromatic hydrocarbon containing in the molecule a linkage selected from the group consisting of ether, ester and amide linkages; and heterocyclic alcohol compounds having a primary alcoholic hydroxyl group and a heterocyclic residue R' selected from the group consisting of pyridoxine, cytidine, arabinocytidine and adenosine; (2) alcohol compounds having a secondary alcoholic hydroxyl group and a C 3 -C 8 aliphatic hydrocarbon group R' which may be substituted by a substituent selected from the group consisting of halogen, amino, mono- or dialkylamino of not more than 3 carbon atoms, and phenyl; and alcohol compounds having a secondary alcoholic hydroxyl group and C 4 -C 6 alicyclic hydrocarbon group R'; and (3) saccharides selected form the group consisting of pentoses having a pentose residue R' and a primary alcoholic hydroxyl group and hexoses having a hexose residue R' and primary alcoholic hydroxyl group, in which the pentose residue R' or the hexose residue R' may be substituted by amino or acetylamino; and phenol glycosides of said saccharides, in the presence of phospholipase DM, said phospholipase DM having the ability to catalyze the formation of a sphingophoispholipid-primary alcohol derivative from a sphingophospholipid and geraniol and the formation of a sphingosphospholipid-secondary alcohol derivative from a sphingopospholipid and 2-butanol, and recovering the reaction product formed.