Patent ID: 6602982
Filing Date: 2003-08-05
Classification: A61K,C07K

Abstract:
A method for producing a glycopeptide of the formula (III): whereinR1â€² is â€”OH; R2â€² is â€”OR7â€² wherein R7â€² is a hydrogen atom or a residue of a saccharide; R3â€² is â€”OR7â€² wherein R7â€² is a hydrogen atom or a residue of a saccharide; R4â€² is â€”CH2OR8â€² wherein R8â€² is a hydrogen atom or a residue of a saccharide, or R4â€² is â€”CH3; R5â€² is a hydrogen atom; R7 is alanine residue; R8 is alanine residue; and R9 is methyl group; â€ƒsaid method comprising: (a) reacting a fluorinated monosaccharide or a fluorinated oligosaccharide of the formula (I) with L-alanyl-L-threonyl-L-alanine having a C-terminal carboxyl group which is protected by a carboxyl-protecting group and an N-terminal amino group which is protected by an amino-protecting group, for a time and under conditions effective to produce a compound of the formula (II), wherein the fluorinated monosaccharide or oligosaccharide of formula (I) is whereinR1 is â€”OR6 wherein R6 is a hydrogen atom or an etheral hydroxyl-protecting group; R2 is â€”OR7â€² wherein R7â€² is a hydrogen atom, an etheral hydroxyl-protecting group, or a residue of a saccharide; R3 is â€”OR7â€² wherein R7â€² is a hydrogen atom, an etheral hydroxyl-protecting group, or a residue of a saccharide; R4 is â€”CH2OR8â€² wherein R8â€² is a hydrogen atom, an etheral hydroxyl-protecting group, or a residue of a saccharide, or R4 is â€”CH3; R5 is a hydrogen atom; and wherein the compound of formula (II) is wherein R1, R2, R3, R4, R5, R7 R8 and R9 are the same as defined above,R10 is said amino-protecting group; R11 is said carboxyl-protecting group; and wherein both said amino-protecting group and said carboxyl-protecting group are removable by hydrogenation; (b) hydrogenating the compound of the formula (II) for a time and under conditions effective to produce the glycopeptide of the formula (III); and (c) isolating the glycopeptide of the formula (III).