Neighboring Group Participation

For Toni Planas, a sabbatical in rural Connecticut has accelerated a sweet collaboration with Mark Peczuh’s research group.

The Glycosidase Team: (L to R) Sergi Pascual, Aditya Pote, Antoni Planas, Mark Peczuh

Carbohydrate chemists are readily familiar with the concept of neighboring group participation (NPG), where the electrons of a nearby functional group accelerate reactions at a given center. A sociological version of NPG operates in the everyday world of scientific collaborations. Antoni Planas (IQS, U. Ramon Llull, Barcelona) has just completed a year-long sabbatical at the University of Connecticut in the laboratory of collaborator Mark Peczuh. His close proximity to Peczuh and his research group has hastened the progress on their project to develop glycosidase enzymes that selectively hydrolyze septanose sugars, making Planas the human equivalent of a participatory neighboring group. Planas, who lived with his family in an old farmhouse on UConn’s main campus, previously hosted Peczuh as a Fulbright Fellow at IQS in 2013 – a visit that initiated the collaboration.

With support from the National Science Foundation and the Spanish Ministry of Economy and Competitiveness, the team is working on a project that leverages Planas’ pre-eminence in bioengineering, especially on carbohydrate active enzymes, with Peczuh’s expertise in the synthesis of ring expanded, seven membered-ring sugars called septanoses. Their collaborative effort to develop a septanose-selective glycosidase requires the synthesis of new chromogenic substrates and some aggressive directed evolution strategies. On the impact of the visit, Peczuh remarked, “Toni’s energy and creativity have pushed the project forward this year. He has an endless supply of ideas and he’s been invaluable as an informal advisor to my grad students.” Things really got going when Toni’s student Sergi Pascual visited in the Spring to work side-by-side with Aditya Pote from the Peczuh group. Sergi got to do some synthesis while he also showed some of the finer points of library screens to Aditya.

Just as with reactivity, neighboring group participation is not a one-off phenomenon for the Planas-Peczuh collaboration. Their experience has convinced them that being close by not only facilitates research productivity, it makes for good fun.

Note: This originally appeared in the Fall 2018 newsletter of the American Chemical Society Division of Carbohydrate Chemistry.