BONNE TERRE, Mo. – With the execution early Wednesday of Leon Vincent Taylor, 2014 ties 1999 for having the most executions in a year in Missouri.

Taylor, 56, who killed a Blue Springs man in 1994 in an Independence gas station robbery, was pronounced dead at 12:22 a.m. at the state prison in Bonne Terre, minutes after receiving a lethal injection.

Taylor shot Robert Newton, 53, to death in front of Newton's 8-year-old stepdaughter. Taylor tried to kill the girl, too, but the gun jammed.

Taylor's fate was sealed Tuesday when Gov. Jay Nixon declined to grant clemency and the U.S. Supreme Court turned down his appeal.

His body covered by a white sheet, Taylor could be seen in the execution chamber talking to family members through the glass in an adjacent room. Once the state started injecting 5 grams of pentobarbital, Taylor's chest heaved for several seconds then stopped. His jaw went slack and he displayed no other movement for the rest of the process.

Four of Taylor's family members sat in a room to his left and looked on without reaction as the drug killed Taylor in about eight minutes. At a time when lethal injections have gone awry in Oklahoma, Ohio and Arizona and taken an extended period to kill an inmate, Taylor's execution went off without any visible complications with the drug or equipment.

In a final statement, Taylor apologized to Newton's family because "our lives had to entwine so tragically" and thanked his family for their support and love.

"I am also sorry to have brought all of you to this point in my life to witness this and/or participate," Taylor said. "Stay strong and keep your heads to the sky."

Speaking to reporters after the execution, Newton's brother, Dennis Smith, noted that it had been about 7,500 days since the killing and said the family has missed Newton every one of them. Smith described Newton as a hard worker, generous and with a memorable laugh. At times, Smith paused to compose himself as tears rolled down his cheeks.

"It would just take a coward to want to hurt someone like him," Smith said.

Taylor's execution was briefly delayed as he sought to have his half brother, Willie Owens, as a witness. Taylor's lawyers filed an appeal four hours before the scheduled execution time and the Missouri Supreme Court granted the request to have the one-time co-defendant in the slaying watch his brother die.

Department of Corrections spokesman Mike O'Connell said Owens ultimately decided not to attend the execution.

Taylor's last meal consisted of eggs, bacon, doughnuts and an orange drink. O'Connell said Taylor later turned down the sedative Valium and the sedative midazolam.

According to court records, Taylor, Owens and his half-sister, Tina Owens, decided to rob a gas station on April 14, 1994. Newton was at the station with his stepdaughter.

Taylor entered the store, drew a gun and told Newton to put $400 in a money bag. Newton complied and Willie Owens took the money to the car.

Taylor then ordered Newton and the child to a back room. Newton pleaded for Taylor not to shoot him in front of the little girl, but Taylor shot him in the head. He tried to kill the girl but the gun jammed, so he locked her in the room and the trio drove away.

Taylor was arrested a week after the crime when police responded to a tips hotline call.