Solid-phase synthesis of human osteocalcin by using a gamma-carboxyglutamic acid derivative.
Human osteocalcin, also called bone Gla protein (BGP), consisting of 49 amino acids with two or three gamma-carboxyglutamate residues, was chemically synthesized for the first time by a novel solid-phase peptide synthesis. An L-enantiomer of N-tert-butyloxycarbonyl-gamma,gamma'-dicyclohexyl-gamma-carboxyglutamic acid was designed, prepared and utilized as a monomeric compound and proven to be useful for the solid-phase peptide synthesis of human osteocalcin. The synthesis and optical resolution of the gamma-carboxyglutamic acid (Gla) derivative are first described, followed by the synthesis and characterization of Gla17-human osteocalcin.
Kurihara
T
T
Tsukuba Medical Development Group, Mitsubishi Petrochemical Co. Ltd., Ibaraki, Japan.
Taniyama
E
E
Hane
M
M
Saito
T
T
Hirose
S
S
Ohashi
S
S
D015055:1-Carboxyglutamic Acid / Q000737:chemistry*; D000595:Amino Acid Sequence; D002851:Chromatography, High Pressure Liquid; D006801:Humans; D008969:Molecular Sequence Data; D015675:Osteocalcin / Q000138:chemical synthesis* / Q000737:chemistry; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013237:Stereoisomerism
D015675:Osteocalcin; D015055:1-Carboxyglutamic Acid