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The synthesis of N ‐[2‐(D‐glucos‐3‐ O ‐yl)propionyl]‐l‐alanine and N ‐[(d‐glucos‐3‐ O ‐yl)acetyl]‐l‐alanine
Author(s) -
Chikashita Hidenori,
Ouchi Tatsuro
Publication year - 1982
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570190501
Subject(s) - chemistry , alanine , residue (chemistry) , moiety , stereochemistry , carbohydrate , organic chemistry , biochemistry , amino acid
N ‐[2‐(D‐Glucos‐3‐ O ‐yl)propionyl]‐L‐alanine ( 7a ) was synthesized, which has a glucose residue instead of N ‐acetylglucosamine residue in the muramyl peptide. N ‐[(D‐Glucos‐3‐ O ‐yl)acetyl]‐L‐alanine ( 7b ) was also synthesized as a glycolyl analog of 7a in order to determine the relationship between the structure of propionyl moiety in the carbohydrate analog ( 7a ) and the adjuvant activity. These simple analogs are compounds prepared for the purpose of introduction into a synthetic polymer with the view of producing polymeric drugs.