Pakistan are in a strong position to wrap up a 2-0 series win over England as two early wickets reduced the tourists to 2-46, a deficit of 238 runs on day four of the third Test in Sharjah.
Alastair Cook (17 not out) and Joe Root (6 not out) were fighting hard against Pakistan's spinners, led by Shoaib Malik who claimed both the wickets on a wearing Sharjah stadium pitch.
Malik, due to quit Test cricket after this match, provided Pakistan early breakthroughs, trapping Moeen Ali (22) leg-before and then bowled Ian Bell (0) in successive overs.
Cook and Root survived confident leg-before appeals off Zulfiqar Babar in the dying moments, much to the relief of the England camp.
England's best chase in all Test cricket is 332 they scored against Australia at Melbourne in 1928 and they have not surpassed more than 209 for victory in the fourth innings in Asia since beating Bangladesh at Dhaka five years ago.
England could have dismissed Pakistan for less than 355 in their second innings and subsequently chasing an easier target had they not dropped two crucial catches; Mohammad Hafeez was spilled on 113 on his way to 151 and Asad Shafiq, who made 46, was dropped on 29.
It was paceman Stuart Broad who led the attack admirably with 3-44 and was ably backed up by James Anderson (2-52) to help England take the last six Pakistan wicket with the second new ball for 126 runs.
It was only through Shafiq and Sarfraz Ahmed's 55-run stand for the seventh wicket that Pakistan's lead soared over 250.
Spinner Samit Patel dismissed the Pakistan wicketkeeper for 36 before Broad had Shafiq to leave Pakistan at 9-354.
England took the second new ball after 81 overs with Pakistan at a lunch score of 4-229 and Broad struck in the fifth over, trapping skipper Misbah-ul-Haq leg before for 38.
Misbah hit two fours and a six and became Broad's 50th wicket in the calendar year in his 13th Test, the best of any player in world cricket in 2015.
Misbah and Hafeez added an invaluable 93 runs for the fifth wicket.
Hafeez, dropped by Broad off his own bowling when on 113, drove Anderson for two to complete the 150-mark, but a run later holed out to spinner Ali at long-on where Bell took a simple catch.
With Hafeez's catch Bell became the eighth English fielder to take 100 catches in Test cricket in his 118th match.
It was a battle of survival for Pakistan in the morning session as England looked for early wickets.
Hafeez survived some anxious moments as leg-spinner Adil Rashid trapped him in front of the wicket with the first ball of the day, after Pakistan resumed on 3-146.
England challenged New Zealand umpire Chris Gaffaney's not out decision but television umpire Paul Reiffel of Australia upheld the verdict.
One ball later Hafeez charged down the wicket against a googly from Rashid but missed the ball completely.
However, wicketkeeper Jonny Bairstow missed a stumping chance and the ball went for four byes.
Hafeez swept Rashid in the next over for a single to reach his century off 169 balls, his second at the Sharjah stadium.