A South Dakota man convicted of fatally stabbing a former doughnut shop co-worker during a 1992 burglary was put to death by lethal injection on Monday night, after the U.S. Supreme Court denied three 11th-hour petitions to stay his execution.

Charles Rhines. South Dakota Department of Corrections via AP / AP

Charles Rhines, 63, whose lawyers argued that his death sentence was tainted by anti-gay bias toward him on the part of jurors, was pronounced dead at 7:39 p.m. CST at the South Dakota State Penitentiary in Sioux Falls, prison spokesman Michael Winder said.

Rhines’ execution had been scheduled for early in the afternoon but was delayed for several hours while state corrections officials awaited word from the U.S. Supreme Court on his final appeals.

All three applications for a stay were rejected by the high court on Monday evening.

Rhines, a high school dropout, was found guilty of murdering Donnivan Schaeffer, 22, an employee at Dig ‘Em Donuts in Rapid City, during a burglary of the doughnut shop on March 8, 1992, weeks after Rhines had quit working there.

Schaeffer was found stabbed to death inside the shop, his hands bound, with about $3,000 in cash and checks missing, according to court documents in the case. A jury sentenced Rhines to death for the killing in January 1993, four days after convicting him.

In an application for a stay filed on Friday, Rhines’ lawyers asked for a court review of evidence that some jurors knew Rhines was gay and believed he would enjoy life in prison with other men if he were spared the death penalty.

The petition, which cited statements by three jurors acknowledging that Rhines’ sexual orientation was an issue for that reason during sentencing deliberations, was denied by the high court without comment.

“It is very sad and profoundly unjust that the state of South Dakota today executed Charles Rhines, a gay man, without any court ever hearing the evidence of gay bias that infected the jury’s decision to sentence him to death,” federal public defender Shawn Nolan said in a statement.

Separately, defense lawyers filed a petition seeking a court order compelling the state to allow medical experts to examine Rhines for evidence of mental illness, such as autism, that might have served as a mitigating factor in his sentencing.

Appellate lawyers also sought to stay the execution while the high court considered Rhines’ request to be put to death by means of a lethal-injection protocol no longer used by South Dakota.

Those two petitions were likewise denied.

Rhines became only the fifth South Dakota inmate put to death since the U.S. Supreme Court upheld the constitutionally of the capital punishment in 1976. He was one of only three inmates on the state’s death row.

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