Synthesis of an N-glucoasparagine analog as a building block for a V3-loop glycopeptide from gp120 of HIV-I.
The preparative synthesis of a new N4-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-L-asparagine mimetic 1, starting from 2-amino-1,5-anhydro-2-deoxy-glucitol hydrochloride and Z-Asp-(OH)-OBn is described. This glycosyl-amino acid unit 1 is expected to show higher stabilities towards in vivo conditions. Further, the use of 1 as building block for the synthesis of modified glycopeptides using solid phase support is reported. The glycopeptide Ac-SXNTRKSIHIGPGRAF-NH2 having sugar-modified Asn2 mimics parts of the V3-loop structure containing the principle neutralizing determinant (PND) of HIV-1 and the naturally conserved glycosylation site within the V3 loop.
Schäfer
A
A
Institut für Organische Chemie der Universität Hamburg, Germany.
Klich
G
G
Schreiber
M
M
Paulsen
H
H
Thiem
J
J
D000117:Acetylglucosamine / Q000031:analogs & derivatives*; D000595:Amino Acid Sequence; D001216:Asparagine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D005947:Glucose / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D006031:Glycosylation; D015699:HIV Envelope Protein gp120 / Q000737:chemistry*; D015497:HIV-1; D008956:Models, Chemical; D018716:Molecular Mimicry; D008969:Molecular Sequence Data; D010446:Peptide Fragments / Q000737:chemistry*
D015699:HIV Envelope Protein gp120; C059762:HIV envelope protein gp120 (305-321); D010446:Peptide Fragments; C000009:N-acetylglucosaminylasparagine; D001216:Asparagine; D005947:Glucose; D000117:Acetylglucosamine