Two-step enzymatic synthesis of maltooligosaccharide esters.
Glucose and maltose esters were synthesised in organic media by employing a lipase (E.C. 3.1.1.3) from Candida antarctica. In a second reaction step, a transglycosylation catalysed by a cyclodextrin glycosyltransferase (E.C. 2.4.1.19) from either Paenibacillus sp. F8 or Bacillus sp. strain no. 169 (DSM 2518) extended the degree of polymerisation (DP) of the carbohydrate moieties of the carbohydrate esters. The donor substrates used were either a cyclodextrin, a maltooligosaccharide or starch. The highest rate of low DP maltooligosaccharide ester formation was obtained when starch was used as glycosyl donor and caproyl maltose as glycosyl acceptor. The structures of two of the products were identified by 1H and 13C NMR and MALDI-TOF MS as capronate monoesters of maltotriose and maltotetraose, with the ester bond at C-6 of the second glucose unit from the reducing end.
Degn
P
P
Department of Civil Engineering, Aalborg University, Denmark.
Larsen
K L
KL
Duus
J O
JO
Petersen
B O
BO
Zimmermann
W
W
D002208:Caproates / Q000737:chemistry / Q000378:metabolism; D002240:Carbohydrate Sequence; D002384:Catalysis; D003505:Cyclodextrins / Q000737:chemistry / Q000378:metabolism; D004952:Esters / Q000138:chemical synthesis*; D005964:Glucosyltransferases / Q000378:metabolism; D006031:Glycosylation; D008049:Lipase / Q000378:metabolism*; D008320:Maltose / Q000031:analogs & derivatives / Q000138:chemical synthesis; D008969:Molecular Sequence Data; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D009844:Oligosaccharides / Q000138:chemical synthesis / Q000378:metabolism*; D013213:Starch / Q000737:chemistry / Q000378:metabolism; D014312:Trisaccharides / Q000138:chemical synthesis
D002208:Caproates; D003505:Cyclodextrins; D004952:Esters; D009844:Oligosaccharides; D014312:Trisaccharides; C021705:maltooligosaccharides; C008317:maltotriose; D008320:Maltose; D013213:Starch; C009819:maltotetraose; D005964:Glucosyltransferases; C019963:cyclomaltodextrin glucanotransferase; D008049:Lipase