N^α-Fmoc-Ser(Ac3-β-D-GlcNAc)-OPfp | 160410-57-1

物质功能分类

化学试剂 - 有机试剂 - 多环化合物

分子结构分类

有机化合物 - 有机氧化合物

中文名称

——

中文别名

——

英文名称

N^α-Fmoc-Ser(Ac3-β-D-GlcNAc)-OPfp

英文别名

(2,3,4,5,6-pentafluorophenyl) (2S)-3-[(2R,3R,4R,5S,6R)-3-acetamido-4,5-diacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoate

N<sup>α</sup>-Fmoc-Ser(Ac3-β-D-GlcNAc)-OPfp化学式

CAS

160410-57-1

化学式

C₃₈H₃₅F₅N₂O₁₃

mdl

——

分子量

822.694

InChiKey

LZLIKDJRORPCKN-WGLUAUJZSA-N

BEILSTEIN

——

EINECS

——

物化性质

沸点：

888.1±65.0 °C(Predicted)
密度：

1.47±0.1 g/cm3(Predicted)

计算性质

辛醇/水分配系数(LogP)：

4
重原子数：

58
可旋转键数：

18
环数：

5.0
sp3杂化的碳原子比例：

0.37
拓扑面积：

191
氢给体数：

2
氢受体数：

18

上下游信息

上游原料

中文名称	英文名称	CAS号	化学式	分子量
——	N^α-(fluoren-9-ylmethoxycarbonyl)-O-(3,4,6-tri-O-acetyl-2-allyloxycarbonylamino-2-deoxy-β-D-glucopyranosyl)-L-serine pentafluorophenyl ester	160410-55-9	C₄₀H₃₇F₅N₂O₁₄	864.731
——	(2,3,4,5,6-pentafluorophenyl) (2S)-3-[(2R,3R,4R,5S,6R)-4,5-diacetyloxy-6-(acetyloxymethyl)-3-(2,2,2-trichloroethoxycarbonylamino)oxan-2-yl]oxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoate	174004-28-5	C₃₉H₃₄Cl₃F₅N₂O₁₄	956.055
——	N-(9-fluorenylmethoxycarbonyl)-(2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranosyl)-L-serine	160067-63-0	C₃₂H₃₆N₂O₁₃	656.643
——	N^α-(fluoren-9-ylmethoxycarbonyl)-O-(3,4,6-tri-O-acetyl-2-deoxy-2-dithiasuccinimido-β-D-glucopyranosyl)-L-serine pentafluorophenyl ester	162894-84-0	C₃₈H₃₁F₅N₂O₁₄S₂	898.793
FMOC-O-叔丁基-L-丝氨酸五氟苯酯	O-tert-butyl-N^α-(fluoren-9-ylmethoxycarbonyl)-L-serine pentafluorophenyl ester	105751-13-1	C₂₈H₂₄F₅NO₅	549.494
N-芴甲氧羰基-L-丝氨酸五氟苯基酯	N^α-(fluoren-9-ylmethoxycarbonyl)-L-serine pentafluorophenyl ester	86061-05-4	C₂₄H₁₆F₅NO₅	493.387
——	3,4,6-tri-O-acetyl-2-allyloxycarbonylamino-2-deoxy-α-D-glucopyranosyl trichloroacetimidate	160410-53-7	C₁₈H₂₃Cl₃N₂O₁₀	533.747
1,3,4,6-TETRA-O-ACETYL-2-DEOXY-2-(2,2,2-TRICHLOROETHOXYCARBONYLAMINO)-Β-D-GLUCOPYRANOSE1,3,4,6-四-O-乙酰基-2-脱氧-2-(2,2,2-三氯乙氧)-Β-D-D-吡喃葡萄糖	1,3,4,6-tetra-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranose	122210-05-3	C₁₇H₂₂Cl₃NO₁₁	522.721
——	3,4,6-Tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl bromide	67124-60-1	C₁₅H₁₉BrCl₃NO₉	543.58
——	3,4,6-tri-O-acetyl-2-N-allyloxycarbonyl-2-amino-2-deoxy-α-D-glucopyranosyl bromide	104655-87-0	C₁₆H₂₂BrNO₉	452.256

反应信息

作为反应物：

描述：

FMOC-L-缬氨酸五氟苯酯、乙酸酐、 N-芴甲氧羰基甘氨酸五氟苯酯、 N^α-Fmoc-Ser(Ac3-β-D-GlcNAc)-OPfp 生成 Ac-Val-Ser(β-D-GlcNAc)-Gly-NH2

参考文献：

名称：

Comparison of N-Dts and N-Aloc in the solid-phase syntheses of O-GlcNAc glycopeptide fragments of RNA-polymerase II and mammalian neurofilaments

摘要：

The application of the glycosylated building blocks N-alpha-Fmoc-Ser(Ac-3-beta-D-GlcNAc)-OPfp 5, N-alpha-Fmoc-Thr(Ac-3-beta-D-GlcNAc)-OPfp 6, N-alpha-Fmoc-Ser(Ac-3-beta-D-GlcNDts)-OPfp 7 and N-alpha-Fmoc-Thr(Ac-3-beta-D-GlcNDts)-OPfp 8 in the solid-phase synthesis-of O-GlcNAc glycopeptides from the C-terminal domain repeating unit of RNA-polymerase II and the NF-L chain of mammalian neurofilaments is described. The removal of the N-dithiasuccinoyl (N-Dts) amino-protecting group was achieved rapidly and quantitatively by thiolysis with 2-sulfanylethanol or dithiothreitol after the incorporation of the building blocks into the resin-bound peptide. The O-GlcNAc glycopeptides 9-11, 13 and 15-21 were synthesised in good yields by comparative studies employing any of the building blocks 5-8. The O-GlcNAc glycopeptides were fully characterised by 1D- and 2D-H-1 NMR spectroscopy and ES-MS.

DOI：

10.1039/p19950002165
作为产物：

描述：

Acetic acid (2R,3S,4R,5R)-3-acetoxy-2-acetoxymethyl-6-bromo-5-(3,5-dioxo-[1,2,4]dithiazolidin-4-yl)-tetrahydro-pyran-4-yl ester 在 3 A molecular sieve 、 silver trifluoromethanesulfonate 、溶剂黄146 、锌作用下，以四氢呋喃、二氯甲烷为溶剂，反应 20.0h，

Nα-Fmoc-Ser(Ac3-β-D-GlcNAc)-OPfp | 160410-57-1