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Arsenal defender Andre Santos joined Brazilian club Gremio on loan until the end of the season on Monday after a miserable spell with the Premier League club.
Santos signed for Arsenal from Turkey's Fenerbahce in a £6.8 million deal on transfer deadline day in August 2011, but the Brazil left-back was unable to adapt to the demands of the English game and was regularly targeted by opponents looking to exploit his error-prone defending.
He also infuriated Gunners manager Arsene Wenger and Arsenal's supporters when he asked former team-mate Robin van Persie to swap shirts at half-time during the 2-1 defeat at Manchester United last November.
The 29-year-old has made just six starts this season and Wenger appeared to admit the transfer had been a mistake when he signed Spain left-back Nacho Monreal from Malaga last month.
"Andre Santos has joined Brazilian side Gremio for the remainder of the 2012/13 season," a statement on Arsenal's website confirmed.
With Kieran Gibbs, Arsenal's other left-back, currently recovering from an injury which is expected to keep him sidelined for two months and Monreal ineligible for the Champions League, Wenger will now have to play centre-back Thomas Vermaelen out of position at left-back when the Gunners face Bayern Munich in the last 16 later this month.
Santos, who has had spells with Brazilian clubs Corinthians, Atletico Mineiro, Flamengo and Figueirense, has made 36 appearances for Arsenal during his time in north London.