Synthesis of cyclic Herpes simplex virus peptides containing 281-284 epitope of glycoprotein D-1 in endo- or exo-position.
We have prepared two types of cyclopeptides containing the 281DPVG284 sequence from the 276-284 region of glycoprotein gD-1 of the Herpes simplex virus (HSV). The syntheses were performed by solid phase methodology using MBHA or BHA resin and orthogonal protection schemes. Head-to-side-chain cyclization included the N-terminal part of the epitope, while side-chain-to-side-chain lactam bridge formation resulted in a peptide containing a C-terminal cycle. Peptides elongated by Cys at the N-terminal of the sequence were also prepared. Boc chemistry using Fmoc and OFm orthogonal protection was applied for on-resin cyclization. Based on the orthogonality of Bzl and cHex esters under a 1 M TMSOTf-thioanisole/TFA cleavage condition, a new approach for the cyclization on BHA-resin has also been developed. Preliminary studies on solution conformation of the cyclic peptides by CD spectroscopy indicated the importance of the location and the size of the cycle within the epitope sequence.
Mezö
G
G
Research Group of Peptide Chemistry, Hungarian Academy of Sciences, Budapest. mezo@para.chem.elte.hu
Majer
Z
Z
Valero
M L
ML
Andreu
D
D
Hudecz
F
F
D000595:Amino Acid Sequence; D002851:Chromatography, High Pressure Liquid; D002942:Circular Dichroism; D000939:Epitopes; D006023:Glycoproteins / Q000138:chemical synthesis; D007769:Lactams / Q000737:chemistry; D013058:Mass Spectrometry; D010455:Peptides / Q000138:chemical synthesis; D017433:Protein Structure, Secondary; D018139:Simplexvirus / Q000737:chemistry*; D014759:Viral Envelope Proteins / Q000138:chemical synthesis*
D000939:Epitopes; D006023:Glycoproteins; D007769:Lactams; D010455:Peptides; D014759:Viral Envelope Proteins