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Synthesis and modification of dibenzylglycine derivatives via the Suzuki-Miyaura cross-coupling reaction

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Title Synthesis and modification of dibenzylglycine derivatives via the Suzuki-Miyaura cross-coupling reaction
 
Creator KOTHA, S
BEHERA, M
 
Subject alpha-amino-acids
peptides
reduction
chirality
esters
combinatorial chemistry
dibenzylglycine derivatives
ethyl isocyanoacetate
suzuki-miyaura coupling
unusual amino acid derivatives
 
Description The objective of this paper is to describe in details of various available methods to prepare C-alpha,C-alpha-dibenzylglycines (Db(z)g) and then include our work involving the synthesis of side chain Db(z)g derivatives. alpha,alpha-Disubstituted amino acids (alpha,alphaAAs) are important members in the family of modified amino acids. Replacement of the alpha-hydrogens of glycine 1 by alkyl groups leads to alpha,alphaAAs. The steric hindrance of the quaternary centre of Aib 2 combined with the helix-forming capacity has attracted the attention of structural biologists and protein crystallographers. Db(z)g 3 is a special structural variant of Aib. The presence of two benzyl groups at C-alpha-position not only impart rigidity to the peptide backbone in which it is incorporated, but also acts as a useful vehicle for studying pi-pi interactions. Although several C-alpha,C-alpha-disubstituted glycines such as C-alpha,C-alpha-diethyl glycine (Deg), C-alpha,C-alpha-dipropyl glycine (Dpg) etc. have been studied in detail, not much has been known about Db(z)g because of limited availability of synthetic procedures. Various Db(z)g derivatives 19a-f have been prepared using ethyl isocyanoacetate 14 as a glycine equivalent (eq.). A useful and simple methodology has been developed using the Suzuki-Miyaura cross-coupling reaction for the modification of Db(z)g derivatives 17d, 19d, 22. Using this 'Building Block Approach' (Accounts of Chemical Research36, 2003, 342) one can generate a variety of Db(z)g derivatives 20a-f and 23a-e, which may find useful applications in combinatorial synthesis and QSAR studies.
 
Publisher BLACKWELL MUNKSGAARD
 
Date 2011-07-19T02:31:48Z
2011-12-26T12:50:57Z
2011-12-27T05:37:12Z
2011-07-19T02:31:48Z
2011-12-26T12:50:57Z
2011-12-27T05:37:12Z
2004
 
Type Article
 
Identifier JOURNAL OF PEPTIDE RESEARCH, 64(2), 72-85
1397-002X
http://dx.doi.org/10.1111/j.1399-3011.2004.00171.x
http://dspace.library.iitb.ac.in/xmlui/handle/10054/5146
http://hdl.handle.net/10054/5146
 
Language en