Solid phase-mediated cyclization of head-to-tail peptides: Problems associated with side chain anchoring
1996; Elsevier BV; Volume: 37; Issue: 24 Linguagem: Inglês
10.1016/0040-4039(96)00803-9
ISSN1873-3581
AutoresMari‐Luz Valero, Ernest Giralt, David Andreu,
Tópico(s)Synthetic Organic Chemistry Methods
ResumoSolid-phase synthesis of cyclic head-to-tail peptides using Boc-based protection schemes and side chain anchoring via the β-carboxyl of Asp can lead to substantial levels of epimerization at the α-carbon of Asp. These problems arise largely from the chemistry used for the incorporation of Boc-Asp(OH)-OFm to the polymer. Several conditions for the attachment of this β-carboxyl to hydroxymethyl or bromomethyl resins have been evaluated, in an attempt to achieve effective, epimerization-free anchorings. The most successful routes involve the use of cesium or zinc salts of Boc-Asp(OH)-OFm.
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