diff --git a/jinja2/utils.py b/jinja2/utils.py
index 49e9e9a..0e67d88 100644
--- a/jinja2/utils.py
+++ b/jinja2/utils.py
@@ -11,6 +11,8 @@
 import re
 import sys
 import errno
+from string import ascii_letters as _letters
+from string import digits as _digits
 try:
     from thread import allocate_lock
 except ImportError:
@@ -19,19 +21,6 @@ from collections import deque
 from itertools import imap
 
 
-_word_split_re = re.compile(r'(\s+)')
-_punctuation_re = re.compile(
-    '^(?P<lead>(?:%s)*)(?P<middle>.*?)(?P<trail>(?:%s)*)$' % (
-        '|'.join(imap(re.escape, ('(', '<', '&lt;'))),
-        '|'.join(imap(re.escape, ('.', ',', ')', '>', '\n', '&gt;')))
-    )
-)
-_simple_email_re = re.compile(r'^\S+@[a-zA-Z0-9._-]+\.[a-zA-Z0-9._-]+$')
-_striptags_re = re.compile(r'(<!--.*?-->|<[^>]*>)')
-_entity_re = re.compile(r'&([^;]+);')
-_letters = 'abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ'
-_digits = '0123456789'
-
 # special singleton representing missing values for the runtime
 missing = type('MissingType', (), {'__repr__': lambda x: 'missing'})()
 
@@ -271,32 +260,61 @@ def urlize(text, trim_url_limit=None, nofollow=False):
     trim_url = lambda x, limit=trim_url_limit: limit is not None \
                          and (x[:limit] + (len(x) >=limit and '...'
                          or '')) or x
-    words = _word_split_re.split(unicode(escape(text)))
+    words = re.split(r"(\s+)", unicode(escape(text)))
     nofollow_attr = nofollow and ' rel="nofollow"' or ''
     for i, word in enumerate(words):
-        match = _punctuation_re.match(word)
+        head, middle, tail = "", word, ""
+        match = re.match(r"^([(<]|&lt;)+", middle)
+
         if match:
-            lead, middle, trail = match.groups()
-            if middle.startswith('www.') or (
-                '@' not in middle and
-                not middle.startswith('http://') and
-                len(middle) > 0 and
-                middle[0] in _letters + _digits and (
-                    middle.endswith('.org') or
-                    middle.endswith('.net') or
-                    middle.endswith('.com')
-                )):
-                middle = '<a href="http://%s"%s>%s</a>' % (middle,
-                    nofollow_attr, trim_url(middle))
-            if middle.startswith('http://') or \
-               middle.startswith('https://'):
-                middle = '<a href="%s"%s>%s</a>' % (middle,
-                    nofollow_attr, trim_url(middle))
-            if '@' in middle and not middle.startswith('www.') and \
-               not ':' in middle and _simple_email_re.match(middle):
-                middle = '<a href="mailto:%s">%s</a>' % (middle, middle)
-            if lead + middle + trail != word:
-                words[i] = lead + middle + trail
+            head = match.group()
+            middle = middle[match.end() :]
+
+        # Unlike lead, which is anchored to the start of the string,
+        # need to check that the string ends with any of the characters
+        # before trying to match all of them, to avoid backtracking.
+        if middle.endswith((")", ">", ".", ",", "\n", "&gt;")):
+            match = re.search(r"([)>.,\n]|&gt;)+$", middle)
+
+            if match:
+                tail = match.group()
+                middle = middle[: match.start()]
+
+        if middle.startswith("www.") or (
+            "@" not in middle
+            and not middle.startswith("http://")
+            and not middle.startswith("https://")
+            and len(middle) > 0
+            and middle[0] in _letters + _digits
+            and (
+                middle.endswith(".org")
+                or middle.endswith(".net")
+                or middle.endswith(".com")
+            )
+        ):
+            middle = '<a href="http://%s"%s>%s</a>' % (
+                middle,
+                nofollow_attr,
+                trim_url(middle),
+            )
+
+        if middle.startswith("http://") or middle.startswith("https://"):
+            middle = '<a href="%s"%s>%s</a>' % (
+                middle,
+                nofollow_attr,
+                trim_url(middle),
+            )
+
+        if (
+            "@" in middle
+            and not middle.startswith("www.")
+            and ":" not in middle
+            and re.match(r"^\S@\w[\w.-]*\.\w$", middle)
+        ):
+            middle = '<a href="mailto:%s">%s</a>' % (middle, middle)
+
+        words[i] = head + middle + tail
+
     return u''.join(words)