Steiman D M, Ridge R J, Matsueda G R
Anal Biochem. 1985 Feb 15;145(1):91-5. doi: 10.1016/0003-2697(85)90331-8.
Solid-phase Edman degradation of synthetic peptidyl-resins has been used advantageously to detect errors of deletion which might occur during Merrifield peptide synthesis. To facilitate complete quantitation of the resulting phenylthiohydantoin(PTH)-amino acids, the PTH derivatives of the following side chain-protected amino acid residues have been synthesized: Arg(Tos), Asp(OBzl), Cys(3,4-(CH3)2-Bzl), Glu(OBzl), Lys(2-ClZ), Ser(Bzl), Thr(Bzl), Tyr(2-BrZ), and Tyr(2,6-Cl2Bzl). For each derivative, a melting point, elemental analysis, and extinction coefficient were obtained. With these new compounds as HPLC standards, an unequivocal assignment and quantification of each side chain protected amino acid was possible. A quantitative analysis was performed for six model peptides with the general formula Ala-X-Leu-Y-Ala-Gly-NHCH2-resin (where X and Y represented different side chain-protected amino acyl residues). We have found solid-phase Edman degradation to be a useful aid for the characterization of peptides when they are used unpurified as synthetic antigens.
固相埃德曼降解合成肽基树脂已被有效地用于检测在梅里菲尔德肽合成过程中可能发生的缺失错误。为便于对所得苯硫基乙内酰脲（PTH）-氨基酸进行完全定量，已合成了以下侧链保护氨基酸残基的PTH衍生物：精氨酸（对甲苯磺酰基）、天冬氨酸（苄酯）、半胱氨酸（3,4-二甲基苄基）、谷氨酸（苄酯）、赖氨酸（2-氯苄氧羰基）、丝氨酸（苄基）、苏氨酸（苄基）、酪氨酸（2-溴苄氧羰基）和酪氨酸（2,6-二氯苄氧羰基）。对于每种衍生物，都获得了熔点、元素分析和消光系数。以这些新化合物作为高效液相色谱标准品，可以明确鉴定和定量每种侧链保护氨基酸。对六种通式为丙氨酸-X-亮氨酸-Y-丙氨酸-甘氨酸-NHCH2-树脂的模型肽进行了定量分析（其中X和Y代表不同的侧链保护氨酰基残基）。我们发现，当肽未纯化用作合成抗原时，固相埃德曼降解是表征肽的有用辅助手段。
