通过脱氢氨基酸的不对称还原合成14C标记的肽。
Synthesis of 14C-labelled peptides by asymmetric reduction of dehydroamino acids.
作者信息
Parnes H, Shelton E J, Huang G T
出版信息
Int J Pept Protein Res. 1986 Oct;28(4):403-10. doi: 10.1111/j.1399-3011.1986.tb03272.x.
The labelled dehydroamino acid, 2-N-acetylamino-3-(2-naphthyl)-3-[14C]-acrylic acid was prepared at 52.8 mCi/mmol from Ba14CO3. Asymmetric reduction of this precursor with hydrogen in the presence of the chiral homogeneous catalyst (S,S) BPPMRh+ afforded N-acetyl-D-3-(2-naphthyl)-3-[14C]-alanine in greater than 98% optical yield. This unnatural amino acid was used in a solution phase synthesis of 2 14C-labelled LHRH analogs, [N-Ac-D-3-[14 C] Nal1 D-p-Cl-Phe2, D-Trp3,D-hArg(Et2)6, D-Ala10] LHRH and [D-3-[14C] Nal6] LHRH having specific activities in excess of 50 mCi/mmol.
标记的脱氢氨基酸，2-N-乙酰氨基-3-(2-萘基)-3-[¹⁴C]-丙烯酸由Ba¹⁴CO₃制备，比活度为52.8 mCi/mmol。在手性均相催化剂(S,S) BPPMRh⁺存在下，用氢气对该前体进行不对称还原，得到光学产率大于98%的N-乙酰-D-3-(2-萘基)-3-[¹⁴C]-丙氨酸。这种非天然氨基酸用于溶液相合成两种¹⁴C标记的促黄体生成素释放激素（LHRH）类似物，即比活度超过50 mCi/mmol的[N-Ac-D-3-[¹⁴C]Nal¹,D-p-Cl-Phe²,D-Trp³,D-hArg(Et₂)⁶,D-Ala¹⁰]LHRH和[D-3-[¹⁴C]Nal⁶]LHRH。
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