Spontaneous cyclization of a chain shortened lysine analog

Ranganathan, S. ; Ranganathan, D. ; Singh, W. P. (1988) Spontaneous cyclization of a chain shortened lysine analog Tetrahedron Letters, 29 (25). pp. 3111-3114. ISSN 0040-4039

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Official URL: http://dx.doi.org/10.1016/0040-4039(88)85099-8

Related URL: http://dx.doi.org/10.1016/0040-4039(88)85099-8


The chain shortened analog of lysine, H2NCH2CH2CH(NHZ)COOR, generated from N-protected glutamine esters, undergoes spontaneous cyclization. The results show that amino acids having H2NCH2CH2 - side chains cannot be supported on tRNA and provides a rationale for keeping the amino group of lysine by as many as four methylenes away from the peptide backbone. In sharp contrast, in the peptide environment, H2NCH2,CH2CH(NHZ)CONHCH(X)COOMe, this unit is stable, thus demonstrating that if they are post transiationally created, can be present as viable side chains in proteins.

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Deposited On:20 Jul 2011 06:41
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