re = /(?:^|,\s*)BIG BOAT\s*(?=,|$)/m
str = 'BIG BOAT , GREEN CAR,BIG BOAT, YELLOW TRUCK, BIG BOAT, AMAZON ECHO, BIG BOAT , BLUE CAR , BIG BOAT BLUE, TABLE, GLASSES, BIG BOAT'
subst = 'TEST'
result = str.gsub(re, subst)
# Print the result of the substitution
puts result
Please keep in mind that these code samples are automatically generated and are not guaranteed to work. If you find any syntax errors, feel free to submit a bug report. For a full regex reference for Ruby, please visit: http://ruby-doc.org/core-2.2.0/Regexp.html