TY - JOUR
T1 - Synthesis of phosphotyrosine‐containing peptides by the solid‐phase method
T2 - A re‐examination of the use of Boc‐Tyr(PO3Bzl2)‐OH
AU - TIAN, ZHENPING
AU - GU, CHING
AU - ROESKE, ROGER W.
AU - ZHOU, MINGMING
AU - VAN ETTEN, ROBERT L.
PY - 1993/8
Y1 - 1993/8
N2 - A practical and convenient procedure for making phosphotyrosine‐containing peptides by the solid‐phase method was developed. Phosphotyrosine was incorporated via Boc‐Tyr(PO3Bzl2)‐OH. The completed peptide was cleaved from the solid support by treatment with 1 M TMSBr‐thioanisole‐TFA. By gel‐phase 31P‐NMR spectroscopy we found that one of the benzyl protecting groups on phosphate was completely removed by two consecutive runs of Boc deprotection with 50% TFA‐DCM. However, the other benzyl group remained intact throughout the synthesis (35 cycles).
AB - A practical and convenient procedure for making phosphotyrosine‐containing peptides by the solid‐phase method was developed. Phosphotyrosine was incorporated via Boc‐Tyr(PO3Bzl2)‐OH. The completed peptide was cleaved from the solid support by treatment with 1 M TMSBr‐thioanisole‐TFA. By gel‐phase 31P‐NMR spectroscopy we found that one of the benzyl protecting groups on phosphate was completely removed by two consecutive runs of Boc deprotection with 50% TFA‐DCM. However, the other benzyl group remained intact throughout the synthesis (35 cycles).
KW - gel‐phase P‐NMR spectroscopy
KW - monodebenzylation
KW - phosphate diester
KW - phosphotyrosine‐containing peptides
KW - solid‐phase peptide synthesis
KW - trimethylsilylbromide
UR - http://www.scopus.com/inward/record.url?scp=0027198289&partnerID=8YFLogxK
U2 - 10.1111/j.1399-3011.1993.tb00491.x
DO - 10.1111/j.1399-3011.1993.tb00491.x
M3 - Article
C2 - 7691774
AN - SCOPUS:0027198289
SN - 0367-8377
VL - 42
SP - 155
EP - 158
JO - International Journal of Peptide and Protein Research
JF - International Journal of Peptide and Protein Research
IS - 2
ER -