Syntheses of dendritic branches based on L-lysine: is the stereochemistry preserved throughout the synthesis?

TY - JOUR

T1 - Syntheses of dendritic branches based on L-lysine: is the stereochemistry preserved throughout the synthesis?

AU - Driffield, M

AU - Goodall, D M

AU - Smith, D K

PY - 2003

Y1 - 2003

N2 - This paper reports the syntheses of individual dendritic branches based on L-lysine and functionalised with either Boc or Bz surface groups. Convergent and divergent synthetic approaches were employed and the preservation of stereochemistry during the syntheses was monitored using polarimetry, NMR and HPLC. In addition, racemic dendritic branches based on D,L-lysine were synthesised for comparative purposes. It was observed that the preservation of stereochemistry in the dendritic peptide was dependent on the method of synthesis, with divergent methodology being preferred. The results are discussed in terms of the known stereochemical outcomes of traditional peptide coupling processes, and are generalised to the synthesis of other dendritic peptides. Such observations about the chirality of dendritic peptides are of relevance to chemists developing dendritic systems for applications where single enantiomer dendrimers would clearly be preferred, such as enantioselective catalysis or pharmaceutical chemistry.

AB - This paper reports the syntheses of individual dendritic branches based on L-lysine and functionalised with either Boc or Bz surface groups. Convergent and divergent synthetic approaches were employed and the preservation of stereochemistry during the syntheses was monitored using polarimetry, NMR and HPLC. In addition, racemic dendritic branches based on D,L-lysine were synthesised for comparative purposes. It was observed that the preservation of stereochemistry in the dendritic peptide was dependent on the method of synthesis, with divergent methodology being preferred. The results are discussed in terms of the known stereochemical outcomes of traditional peptide coupling processes, and are generalised to the synthesis of other dendritic peptides. Such observations about the chirality of dendritic peptides are of relevance to chemists developing dendritic systems for applications where single enantiomer dendrimers would clearly be preferred, such as enantioselective catalysis or pharmaceutical chemistry.

KW - ACID-BASED DENDRIMERS

KW - SOLID-PHASE SYNTHESIS

KW - CHIRAL DENDRIMERS

KW - CHIROPTICAL PROPERTIES

KW - BUILDING-BLOCKS

KW - POLYGLUTAMIC PORPHYRINS

KW - CONVERGENT SYNTHESIS

KW - PEPTIDE DENDRIMERS

KW - FIRST-GENERATION

KW - AMINO-ACIDS

U2 - 10.1039/b304410f

DO - 10.1039/b304410f

M3 - Article

SN - 1477-0520

VL - 1

SP - 2612

EP - 2620

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 14

ER -