Synthesis and application of carbohydrate-derived morpholine amino acids.
The synthesis of series of diversely functionalized epsilon-morpholine amino acids (MAAs, 5a-h) starting from an epsilon-sugar amino acid and following a two-step oxidative glycol cleavage/reductive amination strategy, is described. In an alternative synthetic scheme, diastereoisomerically pure delta-MAAs (12a,b) were obtained. Oligopeptides containing MAAs were prepared either by direct incorporation of a MAA building block or by subjecting a fully assembled SAA-containing peptide to the two-step glycol cleavage/reductive amination procedure.
Grotenbreg
Gijsbert M
GM
Leiden Institute of Chemistry, Gorlaeus Laboratories, P.O. Box 9502, 2300 RA Leiden, The Netherlands.
Christina
Alphert E
AE
Buizert
Annelies E M
AE
van der Marel
Gijsbert A
GA
Overkleeft
Herman S
HS
Overhand
Mark
M
D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D002241:Carbohydrates / Q000138:chemical synthesis / Q000737:chemistry*; D008968:Molecular Conformation; D009025:Morpholines / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
D000596:Amino Acids; D002241:Carbohydrates; D009025:Morpholines