Borussia Dortmund have announced that Germany midfielder Ilkay Gundogan has been ruled out for months and is set to miss Euro 2016.
Gundogan, 25, dislocated his knee cap in training and is now set for an extended period on the sidelines.
He will miss Dortmund's remaining two Bundesliga matches of the season at Frankfurt and at home to Cologne, as well the DFB Pokal final against Bayern Munich.
- Borussia Dortmund (@BVB) May 6, 2016
The playmaker, who has been linked with a summer transfer to Manchester City, has struggled for fitness this season, featuring in just four matches in the last two months.
The Gelsenkirchen-born player is under contract at Dortmund until 2017, but has strongly been linked with a transfer to City ever since his representatives were pictured meeting the club's director of football Txiki Begiristain in Amsterdam in March.
Reports have claimed there is already an agreement in principle to sign Gundogan, but his representatives have said the midfielder has not agreed a deal.
Gundogan missed the 2014 World Cup with a back injury which kept him out of action between August 2013 and October 2014.
Low, who will name his preliminary squad for Euro 2016 on May 17, expressed his regret at losing Gundogan.
"Of course this is a setback for all of us, but above all it is very bitter for Ilkay himself," he said on the German Football Association's website.
"After he was already forced to miss [the World Cup in] Brazil due to injury, now he's going to miss a European Championship which he had such high hopes for.
"He was in great shape and with his dynamism, his vision and his strategic abilities, he played a central role in our plans.
"All of us from the national team wish him first and foremost a speedy return to action."