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Karl Barry Sharpless

From Wikipedia, the free encyclopedia
American chemist and Nobel Laureate (born 1941)

Karl Barry Sharpless
Sharpless in 2018
Born
Karl Barry Sharpless

(1941-04-28)April 28, 1941 (age 84)
Philadelphia, Pennsylvania, U.S.
Alma materDartmouth College (BA)
Stanford University (MS,PhD)
Known for
Spouse
Jan Dueser
(m. 1965)
Awards
Scientific career
FieldsStereochemistry
Institutions
ThesisStudies of the Mechanism of Action of 2,3-oxidosqualene-lanosterol cyclase: Featuring Enzymic Cyclization of Modified Squalene Oxides (1968)
Doctoral advisorEugene van Tamelen
Doctoral studentsM.G. Finn
Other notable studentsUndergrads:Post-docs:

Karl Barry Sharpless (born April 28, 1941) is an Americanstereochemist. He is a two-timeNobel laureate in chemistry, known for his work onstereoselective reactions andclick chemistry.

Sharpless was awarded half of the 2001Nobel Prize in Chemistry "for his work on chirally catalysedoxidation reactions", and one third of the 2022 prize, jointly withCarolyn R. Bertozzi andMorten P. Meldal, "for the development of click chemistry andbioorthogonal chemistry".[1][2] Sharpless is the fifth person (in addition to two organizations) to have twice been awarded a Nobel prize, along withMarie Curie,John Bardeen,Linus Pauling andFrederick Sanger, and the third to have been awarded two prizes in the same discipline (after Bardeen and Sanger).

Early life and education

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Sharpless was born April 28, 1941, inPhiladelphia, Pennsylvania.[3] His childhood was filled with summers at his family cottage on theManasquan River inNew Jersey. This is where Sharpless developed a love for fishing that he would continue throughout his life, spending summers in college working on fishing boats.[4] He graduated fromFriends' Central School in 1959,[5] and continued his studies atDartmouth College, earning anA.B. degree in 1963. Sharpless originally planned to attend medical school after his undergraduate degree, but his research professor convinced him to continue his education in chemistry.[6] He earned hisPh.D. in organic chemistry fromStanford University in 1968 underEugene van Tamelen.[7] He continued post-doctoral work at Stanford University (1968–1969) withJames P. Collman, working onorganometallic chemistry. Sharpless then moved toHarvard University (1969–1970), studying enzymology inKonrad E. Bloch's lab.[6]

Academic career

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Sharpless was a professor at theMassachusetts Institute of Technology (1970–1977, 1980–1990) andStanford University (1977–1980).[8] While at Stanford, Sharpless discoveredSharpless asymmetric epoxidation, which was used to make (+)-disparlure. As of 2023[update], Sharpless led a laboratory atScripps Research.[9]

Research

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Sharpless developed stereoselective oxidation reactions, and showed that the formation of an inhibitor with femtomolar potency can be catalyzed by the enzymeacetylcholinesterase, beginning with an azide and an alkyne. He discovered several chemical reactions which have transformed asymmetric synthesis from science fiction to the relatively routine, including aminohydroxylation, dihydroxylation, and the Sharpless asymmetric epoxidation.[10]

In 2001 he was awarded a half-share of theNobel Prize in Chemistry for his work on chirally catalyzedoxidation reactions (Sharpless epoxidation,Sharpless asymmetric dihydroxylation,Sharpless oxyamination). The other half of the year's Prize was shared betweenWilliam S. Knowles andRyōji Noyori (for their work on stereoselectivehydrogenation).[1]

The term "click chemistry" was coined by Sharpless around the year 2000, and was first fully described by Sharpless,Hartmuth Kolb, andM.G. Finn atThe Scripps Research Institute in 2001.[11][2] This involves a set of highly selective,exothermic reactions which occur under mild conditions; the most successful example is theazide alkyne Huisgen cycloaddition to form1,2,3-triazoles.[12]

As of 2024[update], Sharpless has anh-index of 130 according toScopus.[13]

Awards and honors

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Sharpless is a two-time Nobel laureate. He is a recipient of the 2001 and 2022Nobel Prize in Chemistry for his work on "chirally catalysed oxidation reactions", and "click chemistry", respectively.[1][2]

He was awarded the 2001Wolf Prize in Chemistry together withHenri B. Kagan andRyoji Noyori “for their pioneering, creative and crucial work in developing asymmetric catalysis for the synthesis of chiral molecules, greatly increasing humankind's ability to create new products of fundamental and practical importance”.

In 2019, Sharpless was awarded thePriestley Medal, theAmerican Chemical Society's highest honor, for "the invention of catalytic, asymmetric oxidation methods, the concept of click chemistry and development of the copper-catalyzed version of the azide-acetylene cycloaddition reaction".[5][6] He received theGold Medal of the American Institute of Chemists in 2023.[14]

He is Distinguished University Professor atKyushu University. He holds honorary degrees from theKTH Royal Institute of Technology (1995),Technical University of Munich (1995),Catholic University of Louvain (1996) andWesleyan University (1999).[8]

Personal life

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Sharpless married Jan Dueser in 1965 and they have three children.[10] He was blinded in one eye during a lab accident in 1970 where anNMR tube exploded, shortly after he arrived at MIT as an assistant professor. After this accident, Sharpless stresses "there's simply never an adequate excuse for not wearing safety glasses in the laboratoryat all times."[15]

References

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  1. ^abc"The 2001 Nobel Prize in Chemistry" (Press release).Nobel Foundation. October 10, 2001. RetrievedJanuary 17, 2024.
  2. ^abc"The Nobel Prize in Chemistry 2022". Nobel Foundation. RetrievedOctober 5, 2022.
  3. ^Rogers, Kara, ed. (April 24, 2023)."K. Barry Sharpless".Encyclopedia Britannica. RetrievedJanuary 17, 2024.
  4. ^Sharpless, Barry (December 8, 2001)."Searching For New Reactivity"(PDF).Nobel Prize.
  5. ^abHalford, Bethany (March 31, 2019)."2019 Priestley Medalist K. Barry Sharpless works magic in the world of molecules".Chemical & Engineering News. Vol. 97, no. 13. RetrievedJanuary 17, 2024.
  6. ^abc"K. Barry Sharpless named 2019 Priestley Medalist".Chemical & Engineering News. RetrievedApril 8, 2019.
  7. ^Sharpless, Karl Barry (1968).Studies of the mechanism of action of 2,3-oxidosqualene-lanosterol cyclase: featuring enzymic cyclization of modified squalene oxides (Ph.D.).Stanford University.OCLC 66229398.ProQuest 302369766.
  8. ^abHenderson, Andrea Kovacs (2009).American Men & Women of Science. Farmington Hills, MI: Gale. Cengage Learning. pp. 764.ISBN 9781414433066.
  9. ^"Sharpless Lab - Group Members".Scripps Research. RetrievedJanuary 17, 2024.
  10. ^ab"K. Barry Sharpless".Notable Names Database. Soylent Communications. 2014. RetrievedJuly 12, 2014.
  11. ^Kolb, Hartmuth C.; Finn, M. G.; Sharpless, K. Barry (June 1, 2001). "Click Chemistry: Diverse Chemical Function from a Few Good Reactions".Angewandte Chemie.40 (11):2004–2021.doi:10.1002/1521-3773(20010601)40:11<2004::AID-ANIE2004>3.0.CO;2-5.ISSN 1521-3773.PMID 11433435.
  12. ^Evans, Richard A. (2007). "The Rise of Azide–Alkyne 1,3-Dipolar 'Click' Cycloaddition and its Application to Polymer Science and Surface Modification".Australian Journal of Chemistry.60 (6): 384.doi:10.1071/CH06457.ISSN 0004-9425.
  13. ^"Scopus preview – Sharpless, K. Barry – Author details – Scopus".www.scopus.com. RetrievedOctober 16, 2021.
  14. ^"American Institute of Chemists – Gold Medal Awards".www.theaic.org. RetrievedAugust 22, 2023.
  15. ^Barry Sharpless, Karl (March 11, 1992)."A cautionary tale from the past".MIT News. RetrievedOctober 5, 2022.

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