Missouri has carried out its 72nd execution since 1976.
Michael A Taylor was executed by lethal injection, having been convicted of the rape and murder of 15-year-old Ann Harrison in 1989.
Taylor, 47, was pronounced dead at 12:10 a.m.
Taylor, together with his co-defendant Roderick Nunley pleaded guilty to charges of fatally stabbing Harrison on March 22, 1989, after kidnapping her while she waited for the school bus. They were convicted and sentenced to death.
Taylor spoke briefly on the phone with The Kansas City Star a few hours before the execution, Taylor said he had written a letter to Ann's parents and that a prison official assured him it would be offered to them. In the letter, Taylor said, he expressed "my sincerest apology and heartfelt remorse," and added that he hoped that they would accept it.
There have now been four executions in Missouri since November 2013 using the sedative pentobarbitol.
Taylor's execution came after a day of intense legal challenges in state and federal courts that ended when the U.S. Supreme Court denied Taylor's last request for a stay.
Missouri Gov. Jay Nixon had earlier denied Taylor's request for clemency. After the execution, he made this statement:
"Our thoughts and prayers tonight are with Bob and Janel Harrison, and the other members of Ann Harrison's family, as they remember the 15-year-old child they lost to an act of senseless violence."The execution was witnessed by friends and members of both the Harrison and Taylor families.
On Tuesday night Taylor's family released the following statement:
"The family of Michael Anthony Taylor would like to express their gratitude to all of those who supported Michael over the years. It may be a small victory for the State of Missouri but Michael has won in the end.Questions have been raised about the length of time between the sentence and the execution. Actually, in early 2006, Taylor came within hours of being executed, but the 8th U.S. Circuit Court of Appeals granted a stay.
He has struggled for years with the guilt of not stopping a horrendous crime, and has dedicated much of his time in prison to the memory of Ann Harrison through his work with hospice, tutoring and mentoring inside and outside the prison walls.
Those heartfelt accomplishments will accompany him into the gates of Heaven where he will be joined by his family and beloved angel."
Since then, the drugs used for lethal injections have been difficult to obtain as the manufacturers refused permission for their use for that purpose.
That led to additional legal challenges, including one from Taylor's lawyers over how the drug currently used by Missouri is obtained and manufactured.
Attorneys for the other three prisoners executed in Missouri since November had also challenged its use, but the appeals were denied.