gistfile1.txt

   NSArray *punctuationMarks = [NSArray arrayWithObjects:@".",@",",@"\"",@";",@":",@"!", @"“", @"”", @"?", @"!" , nil];
    NSMutableString *mutableWordString = [wordDescriptor.wordString mutableCopy];
    
    for(NSString *punctuationMark in punctuationMarks) {
        
        
        NSUInteger offset = 0;
        
        while (true) {
            NSRange rangeOfThatPunctuationMark = [mutableWordString rangeOfString:punctuationMark options:NSCaseInsensitiveSearch range:NSMakeRange(offset, mutableWordString.length - offset)];
            
            if(rangeOfThatPunctuationMark.location == NSNotFound) {
                break;
            } else {
                
                NSString *spanToInsert = [NSString stringWithFormat:@"<span class='punctuation'>%@</span>" , punctuationMark];
                
                [mutableWordString replaceCharactersInRange:rangeOfThatPunctuationMark withString:spanToInsert];
                offset += spanToInsert.length;

            }
            
        }
        
    }