The Italian Renaissance painter known as the Master of Santo would surely have been intrigued if he had been able to see a new reinterpretation of one of his paintings, more than 500 years after his death. The era has provided plenty of inspiration for contemporary artists – the work of Jacob Burckhardt, for example – but still, the old master might have been taken aback that the reinterpreter is a street artist living in New York who has reassembled his image with cardboard.

The original painting, Portrait of a Boy, by the master painter and draughtsman whose full name is Agnolo di Domenico del Mazziere (formerly known as the Master of Santo Spirito), is just one of several Renaissance works that have been reinterpreted in a collaboration between Sotheby’s auctioneers and the street art gallery Fat Free Art, based in New York’s Lower East Side.

The Street Masters exhibition, starting on Friday, includes work by a host of internationally renowned street artists, while the masters that inspired them will be auctioned by Sotheby’s on 8 June.

Those taking part include Japanese street artist Lady Aiko, who is based in Brooklyn; UK artists Nick Walker, Fanakapan and Zeus; Spanish artist Belin and others. Jon Satin, co-owner of Fat Free Art, said he had approached Sotheby’s about the idea when they had visited one of their street art exhibitions and found them receptive. “Their masters auctions on the high end sell for hundreds of thousands and millions,” said Satin, and the hope was the collaboration could help widen the audiences of both genres of art.

Satin said Sotheby’s had suggested the urban artists could add “their own spin” to the works, which didn’t need to be a literal interpretation. “And the street artists loved it,” said Satin, whose gallery was helped by the independent urban art network @wherethereswalls to bring so many international artists together. “They jumped at it … There’s long been this interest. It’s the kind of thing Banksy did with the Girl with the Pearl Earring,” said Satin, referring to Banksy’s Girl with the Pierced Eardrum in Bristol from several years ago.

Satin said: “Everybody is now embracing street art, even those on the sidelines who may have been naysayers can’t deny it after the [Jean-Michel] Basquiat sale the other week,” when one of his skull paintings sold for $110.5m at auction in New York.

David Pollack, a specialist in old master paintings at Sotheby’s said it was their goal to “introduce a new generation of art lovers to the rich and fascinating visual history of painting”.

Pollack said: “When seen through the lens of street art and artists, our paintings take on a fresh energy, and this collaboration is a physical interpretation of that dynamism.

“In this new context, old masters suddenly appear new again, much in the way I imagine they looked and felt to viewers when they were first created centuries ago. The people who traditionally visit our respective spaces rarely interact, so we’re excited to mix things up and facilitate new ways of looking at art.”

Satin said one of the most popular images with the urban artists to reinterpret was a painting Sotheby’s is auctioning called Lucretia, by Workshop of Lucas Cranach the Elder, a 16th-century German Renaissance painter.

Among those inspired by Lucretia was Spanish street artist Miguel Angel Belinchon Bujes, known as Belin, who has described his work as “post-neocubism” and cited Picasso as an inspiration. Of his piece for the project, he said: “I kept using vivid colors and a mix in textures,” and that with a combination of techniques he hoped to bring a “new dynamic” to the work.

Other reinterpretations include the Portrait of a Boy in cardboard by Thomas Albertini, who was born in Milan and now lives in New York. Fat Free Art opened last year and has had previous shows including the New York street artist Dain’s first solo gallery show and the exhibition Fem-in-ism, celebrating the current wave of woman-led activism