Sounds like an encoding problem. Is your string utf-8? (Encode, $decoded_str = decode('utf-8', $str)) Did you use utf8 to get your literals parsed as such?
(You see, those fancy apostrophes are represented as three bytes. If Perl thinks we're still in ascii-land (binary-land), it sees the transliteration as tr/\xe2\x80\x99/'/ -- effectively changing any of those three bytes to an apostrophe.)
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