Premium
Enzymatic Cleavage of N ‐Phenylacetyl‐Protected Ethanolamine Phosphates
Author(s) -
van Straten Nicole C. R.,
Duynstee Howard I.,
de Vroom Erik,
van der Marel Gijsbert A.,
van Boom Jacques H.
Publication year - 1997
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.199719970625
Subject(s) - chemistry , disaccharide , ethanolamine , stereochemistry , dimer , protecting group , phosphonate , enzyme , reagent , cleavage (geology) , organic chemistry , alkyl , geotechnical engineering , fracture (geology) , engineering
Immobilized penicillin‐G acylase mediated removal of the N ‐phenylacetyl protective group in ethanolamine phosphates 7 and 9 furnished compounds 8 and 10 , respectively. Deblocking of N ‐phenylacetyl‐protected ethanolamine phosphate heptosyl disaccharide 22 , a protected spacer‐containing fragment of the inner‐core lipopolysaccharide region of Neisseria meningitidis , immunotype L3 was readily accomplished with penicillin‐G acylase, yielding target dimer 2 . Disaccharide 22 was accessible by elongation of ethyl 1‐thio‐ L ‐ glycero ‐α‐ D ‐ manno ‐heptopyranosyl donor 13 with acceptor 14 under the influence of N ‐iodosuccinimide/triflic acid. Protective group manipulations, phosphorylation with the reagent 2‐cyanoethyl 2‐(phenylacetylamino)ethyl N,N ‐diisopropylphosphoramidite ( 5 ) and deprotection furnished LD ‐Hep p dimer 22 .
Accelerating Research
Robert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom
Address
John Eccles HouseRobert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom