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水杨醛
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Fmoc-Thr(α-Ac3GalNAc)-OtBu | 120173-56-0

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

Fmoc-Thr(α-Ac3GalNAc)-OtBu

英文别名

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

CAS

120173-56-0

化学式

C₃₇H₄₆N₂O₁₃

mdl

——

分子量

726.778

InChiKey

MXDXWMQDZUVOIK-XCYCQXQLSA-N

BEILSTEIN

——

EINECS

——

物化性质

沸点：

851.8±65.0 °C(Predicted)
密度：

1.30±0.1 g/cm3(Predicted)

计算性质

辛醇/水分配系数(LogP)：

3.3
重原子数：

52
可旋转键数：

18
环数：

4.0
sp3杂化的碳原子比例：

0.51
拓扑面积：

191
氢给体数：

2
氢受体数：

13

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-[(9H-fluoren-9-ylmethoxy)carbonyl]-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-L-threonine-tert-butyl ester	120791-77-7	C₃₅H₄₂N₄O₁₂	710.738
——	O-(Acetoacetyl)-N-(9-fluorenylmethoxycarbonyl)-L-threonin-tert-butylester	120792-32-7	C₂₇H₃₁NO₇	481.546
——	O-(Acetoacetyl)-N-(9-fluorenylmethoxycarbonyl)-L-threonin	120791-75-5	C₂₃H₂₃NO₇	425.438
Nα-[(9H-芴-9-基甲氧基)羰基]-L-苏氨酸叔丁酯	N-fluorenylmethoxycarbonyl-threonine-tert-butyl ester	120791-76-6	C₂₃H₂₇NO₅	397.471
——	3,4,6-tri-O-acetyl-2-azido-2-deoxy-D-galactopyranosyl trichloroacetimidate	167939-15-3	C₁₄H₁₇Cl₃N₄O₈	475.67
2-叠氮-D-半乳糖四乙酸酯	1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-D-galactopyranose	84278-00-2	C₁₄H₁₉N₃O₉	373.32
——	3,4,6-tri-O-acetyl-2-azido-2-deoxy-α/β-D-galactopyranosyl nitrate	196398-25-1	C₁₂H₁₆N₄O₁₀	376.28
——	3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl nitrate	68733-05-1	C₁₂H₁₆N₄O₁₀	376.28

下游产品

中文名称	英文名称	CAS号	化学式	分子量
N-芴甲氧羰基-O-beta-(2-乙酰氨基-2-脱氧-3,4,6-三-O-乙酰基-alpha-D-吡喃半乳糖基)-L-苏氨酸	N-(9H-fluoren-9-yl)methoxycarbonyl-O-(3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-α-D-galactopyranosyl)-L-threonine	116783-35-8	C₃₃H₃₈N₂O₁₃	670.67
——	N^α-(fluoren-9-ylmethoxycarbonyl)-O-[O-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)-(1->3)-2-acetamido-4,6-di-O-acetyl-2-deoxy-α-D-galactopyranosyl]-L-threonine tert-butyl ester	195976-10-4	C₄₉H₆₂N₂O₂₁	1015.03
——	N^α-fluoren-9-ylmethoxycarbonyl-O-[O-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)-(1->3)-2-acetamido-4,6-di-O-acetyl-2-deoxy-α-D-galactopyranosyl]-L-threonine	125760-33-0	C₄₅H₅₄N₂O₂₁	958.925
——	N-Fmoc-(O-N-acetylgalactosaminyl)threonine tert-butyl ester	189561-75-9	C₃₁H₄₀N₂O₁₀	600.666
——	O-(2-Acetamido-3,4,6-tri-O-acetyl-2-desoxy-α-D-galactopyranosyl)-N-(9-fluorenylmethoxycarbonyl)-L-threonyl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-α-D-galactopyranosyl)-L-serin-tert-butylester	120173-62-8	C₅₄H₇₀N₄O₂₃	1143.16
——	methyl (2R,4S,5R,6R)-5-acetamido-2-[[(2R,3R,4R,5R,6S)-5-acetamido-3,4-diacetyloxy-6-[(2R,3S)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-4-[(2-methylpropan-2-yl)oxy]-4-oxobutan-2-yl]oxyoxan-2-yl]methoxy]-4-acetyloxy-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate	189561-81-7	C₅₅H₇₁N₃O₂₄	1158.17
——	O-(2-Acetamido-3,4,6-tri-O-acetyl-2-desoxy-α-D-galactopyranosyl)-N-(9-fluorenylmethoxycarbonyl)-L-threonyl-L-alanin-tert-butylester	120173-85-5	C₄₀H₅₁N₃O₁₄	797.857
——	methyl (2R,4S,5R,6R)-5-acetamido-2-[[(2R,3R,4R,5R,6S)-5-acetamido-6-[(2R,3S)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-4-[(2-methylpropan-2-yl)oxy]-4-oxobutan-2-yl]oxy-3,4-dihydroxyoxan-2-yl]methoxy]-4-acetyloxy-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate	189561-76-0	C₅₁H₆₇N₃O₂₂	1074.1
——	O-(2-Acetamido-3,4,6-tri-O-acetyl-2-desoxy-α-D-galactopyranosyl)-N-(9-fluorenylmethoxycarbonyl)-L-threonyl-O-tert-butyl-L-seryl-O-tert-butyl-L-serin-tert-butylester	120792-01-0	C₅₁H₇₂N₄O₁₇	1013.15
——	N-(N-(((9H-fluoren-9-yl)methoxy)carbonyl)-O-((2S,3R,4R,5R,6R)-3-acetamido-4,5-diacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yl)-L-threonyl)-O-((2S,3R,4R,5R,6R)-3-acetamido-4,5-diacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yl)-L-serine	120204-28-6	C₅₀H₆₂N₄O₂₃	1087.06
——	N-(fluoren-9-ylmethoxycarbony)-O-{O-[methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosyl)onate]-(2->6)-(2-acetamido-3,4-di-O-acetyl-2-deoxy-α-D-galactopyranosyl)}-L-threonine	189561-77-1	C₅₁H₆₃N₃O₂₄	1102.07
——	Fmoc-Thr(β-6-O-Bn-Ac3Gal-(1-3)-α-4,6-O-Bzn-GalNAc)-OtBu	638207-71-3	C₅₇H₆₆N₂O₁₈	1067.15
——	Fmoc-Thr(β-6-O-Bn-Gal-(1-3)-α-4,6-O-Bzn-GalNAc)-OtBu	638207-72-4	C₅₁H₆₀N₂O₁₅	941.042
——	Fmoc-Thr-(α-4,6-O-Bzn-GalNAc)-OtBu	638207-70-2	C₃₈H₄₄N₂O₁₀	688.775
——	N-(9H-fluoren-9-yl)-methoxycarbonyl-O-{2-acetamido-3,4-di-O-acetyl-2-deoxy-6-O-[benzyl-(5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-glycero-D-galacto-2-nonulopyranosyl)onat]-α-D-galactopyranosyl}-L-threonine tert-butyl ester	330846-49-6	C₆₁H₇₅N₃O₂₄	1234.27
——	N-(9H-fluoren-9-yl)-methoxycarbonyl-O-{2-acetamido-2-deoxy-6-O-[benzyl-(5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-glycero-D-galacto-2-nonulopyranosyl)onat]-α-D-galactopyranosyl}-L-threonine tert-butyl ester	330846-48-5	C₅₇H₇₁N₃O₂₂	1150.2
——	Fmoc‐Thr‐(αAc4NeuNAcCOOBn‐(2→6)‐αGalNAc)-OH	330846-50-9	C₅₇H₆₇N₃O₂₄	1178.16
——	(2S,3R)-3-[(2S,4aR,6S,7R,8R,8aR)-7-Acetylamino-8-hydroxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid tert-butyl ester	673476-38-5	C₃₉H₄₆N₂O₁₁	718.801
——	O-(2-Acetamido-3,4,6-tri-O-acetyl-2-desoxy-α-D-galactopyranosyl)-N-acetyl-L-threonyl-tert-butylester	126133-83-3	C₂₄H₃₈N₂O₁₂	546.572
——	N-Benzyloxycarbonyl-L-alanyl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-α-D-galactopyranosyl)-L-threonin-tert-butylester	126133-42-4	C₃₃H₄₇N₃O₁₄	709.748
——	N-Benzyloxycarbonyl-L-valyl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-α-D-galactopyranosyl)-L-threonin-tert-butylester	126133-34-4	C₃₅H₅₁N₃O₁₄	737.802
——	O-(2-Acetamido-3,4,6-tri-O-acetyl-2-desoxy-α-D-galactopyranosyl)-L-threonin-tert-butylester	120791-78-8	C₂₂H₃₆N₂O₁₁	504.535
——	O-(2-Acetamido-3,4,6-tri-O-acetyl-2-desoxy-α-D-galactopyranosyl)-N-acetyl-L-threonin	126133-85-5	C₂₀H₃₀N₂O₁₂	490.464
——	N-Benzyloxycarbonyl-L-alanyl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-α-D-galactopyranosyl)-L-threonin	126133-43-5	C₂₉H₃₉N₃O₁₄	653.64
——	N-(Benzyloxycarbonyl)-L-alanyl-L-prolyl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-α-D-galactopyranosyl)-L-threonin-tert-butylester	120791-83-5	C₃₈H₅₄N₄O₁₅	806.865
——	L-Alanyl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-α-D-galactopyranosyl)-L-threonin	126133-52-6	C₂₁H₃₃N₃O₁₂	519.506
——	N-Benzyloxycarbonyl-L-valyl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-α-D-galactopyranosyl)-L-threonin	126133-35-5	C₃₁H₄₃N₃O₁₄	681.694
——	N-Benzyloxycarbonyl-L-alanyl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-α-D-galactopyranosyl)-L-threonyl-L-valin-tert-butylester	126133-44-6	C₃₈H₅₆N₄O₁₅	808.88
——	O-(2-Acetamido-3,4,6-tri-O-acetyl-2-desoxy-α-D-galactopyranosyl)-L-threonyl-O-tert-butyl-L-seryl-O-tert-butyl-L-serin-tert-butylester	120792-02-1	C₃₆H₆₂N₄O₁₅	790.906
——	N-(Benzyloxycarbonyl)-L-alanyl-L-prolyl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-α-D-galactopyranosyl)-L-threonin	120173-73-1	C₃₄H₄₆N₄O₁₅	750.757
——	N-(Benzyloxycarbonyl)-L-alanyl-L-prolyl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-α-D-galactopyranosyl)-L-threonyl-O-tert-butyl-L-serin-tert-butylester	120791-84-6	C₄₅H₆₇N₅O₁₇	950.05
——	N-(Benzyloxycarbonyl)-L-alanyl-L-prolyl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-α-D-galactopyranosyl)-L-threonyl-O-tert-butyl-L-seryl-O-tert-butyl-L-serin-tert-butylester	120792-03-2	C₅₂H₈₀N₆O₁₉	1093.24
——	N-(Benzyloxycarbonyl)-L-alanyl-L-prolyl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-α-D-galactopyranosyl)-L-threonyl-O-tert-butyl-L-seryl-O-tert-butyl-L-seryl-O-tert-butyl-L-serin-tert-butylester	120791-98-2	C₅₉H₉₃N₇O₂₁	1236.42
——	O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl)-L-threonine	133477-83-5	C₁₈H₂₈N₂O₁₁	448.427
——	N-Benzyloxycarbonyl-L-alanyl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-α-D-galactopyranosyl)-L-threonyl-L-prolin-tert-butylester	126133-47-9	C₃₈H₅₄N₄O₁₅	806.865
——	N-Benzyloxycarbonyl-L-alanyl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-α-D-galactopyranosyl)-L-threonyl-L-prolyl-L-prolin-tert-butylester	126133-49-1	C₄₃H₆₁N₅O₁₆	903.981
——	L-Alanyl-L-prolyl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-α-D-galactopyranosyl)-L-threonin	120791-85-7	C₂₆H₄₀N₄O₁₃	616.623
——	N-Benzyloxycarbonyl-L-alanyl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-α-D-galactopyranosyl)-L-threonyl-L-valin	126133-45-7	C₃₄H₄₈N₄O₁₅	752.773
——	N-Benzyloxycarbonyl-L-valyl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-α-D-galactopyranosyl)-L-threonyl-glycin-benzylester	126133-38-8	C₄₀H₅₂N₄O₁₅	828.871
——	L-Alanyl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-α-D-galactopyranosyl)-L-threonyl-L-valin	126133-46-8	C₂₆H₄₂N₄O₁₃	618.638
——	N-Benzyloxycarbonyl-L-valyl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-α-D-galactopyranosyl)-L-threonyl-L-prolin-benzylester	126133-36-6	C₄₃H₅₆N₄O₁₅	868.935
——	N-Benzyloxycarbonyl-L-alanyl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-α-D-galactopyranosyl)-L-threonyl-L-prolin	126133-48-0	C₃₄H₄₆N₄O₁₅	750.757
——	(S)-2-[(2S,3R)-2-Amino-3-((2S,3R,4R,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-butyrylamino]-propionic acid	116747-45-6	C₂₁H₃₃N₃O₁₂	519.506
——	N-Benzyloxycarbonyl-L-alanyl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-α-D-galactopyranosyl)-L-threonyl-L-prolyl-L-prolin	126133-50-4	C₃₉H₅₃N₅O₁₆	847.874
——	L-Valyl-O-(2-acetamido-3-tri-O-acetyl-2-desoxy-α-D-galactopyranosyl)-L-threonyl-glycin	126133-39-9	C₂₅H₄₀N₄O₁₃	604.612
——	L-Alanyl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-α-D-galactopyranosyl)-L-threonyl-L-prolin	126133-55-9	C₂₆H₄₀N₄O₁₃	616.623
——	L-Alanyl-L-prolyl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-α-D-galactopyranosyl)-L-threonyl-L-serin	120791-86-8	C₂₉H₄₅N₅O₁₅	703.701
——	L-Alanyl-L-prolyl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-α-D-galactopyranosyl)-L-threonyl-L-seryl-L-seryl-L-serin	120791-99-3	C₃₅H₅₅N₇O₁₉	877.857
——	L-Alanyl-L-prolyl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-α-D-galactopyranosyl)-L-threonyl-L-seryl-L-serin	120792-04-3	C₃₂H₅₀N₆O₁₇	790.779
——	N-Acetyl-L-valyl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-α-D-galactopyranosyl)-L-threonyl-L-prolin	126133-89-9	C₃₀H₄₆N₄O₁₄	686.714
——	L-Valyl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-α-D-galactopyranosyl)-L-threonyl-L-prolin	126133-37-7	C₂₈H₄₄N₄O₁₃	644.676
——	L-Alanyl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-α-D-galactopyranosyl)-L-threonyl-L-prolyl-L-prolin	126133-51-5	C₃₁H₄₇N₅O₁₄	713.739
——	N-Acetyl-L-valyl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-α-D-galactopyranosyl)-L-threonyl-L-prolinamid	126133-95-7	C₃₀H₄₇N₅O₁₃	685.729
——	Boc-Thr(α-GalNAc)-OH	1271737-90-6	C₁₇H₃₀N₂O₁₀	422.433
——	O-(2-Acetamido-2-desoxy-α-D-galactopyranosyl)-N-acetyl-L-threonin-tert-butylester	126133-84-4	C₁₈H₃₂N₂O₉	420.46
——	L-Alanyl-O-(2-acetamido-2-desoxy-α-D-galactopyranosyl)-L-threonin	126133-53-7	C₁₅H₂₇N₃O₉	393.394
——	3-O-(2-acetamido-2-deoxy-α-D-galactopyranosyl)-N-acetyl-L-threonine	88498-16-2	C₁₄H₂₄N₂O₉	364.353
——	L-Alanyl-L-prolyl-O-(2-acetamido-2-desoxy-α-D-galactopyranosyl)-L-threonin	120792-24-7	C₂₀H₃₄N₄O₁₀	490.511
——	L-Alanyl-O-(2-acetamido-2-desoxy-α-D-galactopyranosyl)-L-threonin-L-valin	126133-54-8	C₂₀H₃₆N₄O₁₀	492.527
——	L-Alanyl-glycyl-L-alanyl-glycyl-O-(2-acetamido-2-desoxy-α-D-galactopyranosyl)-L-threonyl-L-alanin	116747-53-6	C₂₅H₄₃N₇O₁₃	649.656
——	L-Alanyl-O-(2-acetamido-2-desoxy-α-D-galactopyranosyl)-L-threonyl-L-prolin	126133-56-0	C₂₀H₃₄N₄O₁₀	490.511
——	N-Acetyl-L-valyl-O-(2-acetamido-2-desoxy-α-D-galactopyranosyl)-L-threonyl-L-prolin	126133-90-2	C₂₄H₄₀N₄O₁₁	560.602
——	L-Alanyl-O-(2-acetamido-2-desoxy-α-D-galactopyranosyl)-L-threonyl-L-prolyl-L-prolin	126133-57-1	C₂₅H₄₁N₅O₁₁	587.627
——	L-Alanyl-L-prolyl-O-(2-acetamido-2-desoxy-α-D-galactopyranosyl)-L-threonyl-L-seryl-L-seryl-L-serin	120792-27-0	C₂₉H₄₉N₇O₁₆	751.745
——	L-Alanyl-L-prolyl-O-(2-acetamido-2-desoxy-α-D-galactopyranosyl)-L-threonyl-L-seryl-L-serin	120792-26-9	C₂₆H₄₄N₆O₁₄	664.667
——	L-Alanyl-L-prolyl-O-(2-acetamido-2-desoxy-α-D-galactopyranosyl)-L-threonyl-L-serin	120792-25-8	C₂₃H₃₉N₅O₁₂	577.589
——	L-Valyl-O-(2-acetamido-2-desoxy-α-D-galactopyranosyl)-L-threonyl-L-prolin	126133-40-2	C₂₂H₃₈N₄O₁₀	518.565
——	L-Alanyl-O-(2-acetamido-2-desoxy-α-D-galactopyranosyl)-L-threonyl-L-valyl-O-(2-acetamido-2-desoxy-α-D-galactopyranosyl)-L-threonyl-L-alanyl-glycin	116747-63-8	C₃₇H₆₄N₈O₁₉	924.957
——	L-Valyl-O-(2-acetamido-2-desoxy-α-D-galactopyranosyl)-L-threonyl-glycin	126133-41-3	C₁₉H₃₄N₄O₁₀	478.5
——	N-Acetyl-L-valyl-O-(2-acetamido-2-desoxy-α-D-galactopyranosyl)-L-threonyl-L-prolinamid	126133-98-0	C₂₄H₄₁N₅O₁₀	559.617
——	O-(2-Acetamido-2-desoxy-α-D-galactopyranosyl)-L-threonyl-L-alanin	120173-86-6	C₁₅H₂₇N₃O₉	393.394

反应信息

作为反应物：

描述：

Fmoc-Thr(α-Ac3GalNAc)-OtBu 在 sodium methylate 作用下，以甲醇、 1,2-二氯乙烷为溶剂，反应 15.0h，生成 N-[(9H-fluoren-9-yl)-methoxycarbonyl]-O-[O-(2'',3'',4'',6''-tetra-O-acetyl-β-D-galactopyranosyl)-(1''-3)-(2-azido-4O,6O-benzylidene-2-deoxy-α-D-galactopyranosyl)]-L-threonine tert-butyl ester

参考文献：

名称：

通过表达丝氨酸连接揭示白细胞介素-2糖蛋白的功能意义

摘要：

天然存在的白细胞介素 2 (IL-2) 是一种多效性糖蛋白，通过控制 T 细胞的分化和稳态来调节免疫反应。非糖基化 IL-2 已在临床环境中使用了 30 年。然而，天然 IL-2 的O-聚糖的功能仍然难以捉摸。在此，为了强调这个问题，我们报告了一种高效的半合成同质糖基化 IL-2 与多种糖蛋白形式的数毫克规模。糖肽片段通过化学合成制备，然后通过重组片段与重组片段融合丝氨酸连接，在一次操作中生成所需的糖蛋白。同源糖蛋白库的生物学评价表明，IL-2在激活个体T细胞亚群中的活性是聚糖依赖性的，从而突出了进一步改进当前临床医学的可能性。

DOI：

10.1002/cjoc.202100914
作为产物：

描述：

3,4,6-tri-O-acetyl-2-azido-2-deoxy-D-galactopyranose 在 potassium carbonate 、锌作用下，以四氢呋喃、乙醚、二氯甲烷为溶剂，反应 26.0h，生成 Fmoc-Thr(α-Ac3GalNAc)-OtBu

参考文献：

名称：

通过表达丝氨酸连接揭示白细胞介素-2糖蛋白的功能意义

摘要：

天然存在的白细胞介素 2 (IL-2) 是一种多效性糖蛋白，通过控制 T 细胞的分化和稳态来调节免疫反应。非糖基化 IL-2 已在临床环境中使用了 30 年。然而，天然 IL-2 的O-聚糖的功能仍然难以捉摸。在此，为了强调这个问题，我们报告了一种高效的半合成同质糖基化 IL-2 与多种糖蛋白形式的数毫克规模。糖肽片段通过化学合成制备，然后通过重组片段与重组片段融合丝氨酸连接，在一次操作中生成所需的糖蛋白。同源糖蛋白库的生物学评价表明，IL-2在激活个体T细胞亚群中的活性是聚糖依赖性的，从而突出了进一步改进当前临床医学的可能性。

DOI：

10.1002/cjoc.202100914

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文献信息

Synthesis of tumor-associated MUC1-glycopeptides and their multivalent presentation by functionalized gold colloids

作者：Isabella Tavernaro、Sebastian Hartmann、Laura Sommer、Heike Hausmann、Christian Rohner、Martin Ruehl、Anja Hoffmann-Roeder、Sabine Schlecht

DOI：10.1039/c4ob01339e

日期：——

The authors present the synthesis of novel MUC1-glycopeptide antigens and their multivalent presentation by gold colloids. Their biological activity was tested in a dot-blot immunoassay experiment.

作者们介绍了新型MUC1-糖肽抗原的合成以及它们在金胶体中的多价展示。它们的生物活性在点印免疫分析实验中得到了测试。
Synthetic MUC1 Antitumor Vaccine with Incorporated 2,3-Sialyl-T Carbohydrate Antigen Inducing Strong Immune Responses with Isotype Specificity

作者：David Straßburger、Markus Glaffig、Natascha Stergiou、Sabrina Bialas、Pol Besenius、Edgar Schmitt、Horst Kunz

DOI：10.1002/cbic.201800148

日期：2018.6.4

On target: Synthetic antitumor vaccines based on human tumor‐associated MUC1 glycopeptides incorporating 2,3‐sialyl T antigen and Tn antigen induce a strong immune response in BALB/c and C57BL/6 mice with antibody subtype selectivity. The results suggest that glycosylation in the PDTRP domain positively effects the immunological response.

靶向治疗：基于人类肿瘤相关MUC1糖肽的合成抗肿瘤疫苗，结合了2,3-唾液酸 T抗原和Tn抗原，可在BALB / c和C57BL / 6小鼠中产生强烈的免疫应答，具有抗体亚型选择性。结果表明PDTRP结构域中的糖基化积极影响免疫反应。
Biomimetic Synthesis of the Tumor-Associated (2,3)-Sialyl-T Antigen and Its Incorporation into Glycopeptide Antigens from the Mucins MUC1 and MUC4

作者：Sebastian Dziadek、Constanze Brocke、Horst Kunz

DOI：10.1002/chem.200400228

日期：2004.9.6

Among the tumor-associated saccharide antigens, the (2,3)-sialyl-T antigen has been identified as the most abundant glycan, found in several different carcinoma cell lines. According to a linear biomimetic strategy, the (2,3)-sialyl-T antigen was synthesized by a stepwise glycan chain extension of a protected galactosamine-threonine precursor. For the construction of immunostimulating antigens combining

上皮肿瘤细胞上的糖蛋白通常表现出异常的糖基化特征。由葡糖胺转移的下调和唾液酸化过早导致的聚糖侧链的不完全形成导致另外的肽表位，其在粘蛋白型糖蛋白中变得可为免疫系统所接近。这些癌症特异性结构改变被认为是对肿瘤细胞进行选择性免疫攻击的有前途的基础。在与肿瘤相关的糖抗原中，（2,3）-唾液酸-T抗原已被确定为最丰富的聚糖，存在于几种不同的癌细胞系中。根据线性仿生策略，通过保护的半乳糖胺-苏氨酸前体的逐步聚糖链延伸合成（2,3）-唾液酸-T抗原。
Synthesis of Tn/T Antigen MUC1 Glycopeptide BSA Conjugates and Their Evaluation as Vaccines

作者：Hui Cai、Zhi-Hua Huang、Lei Shi、Peng Zou、Yu-Fen Zhao、Horst Kunz、Yan-Mei Li

DOI：10.1002/ejoc.201100304

日期：2011.7

The tumor-associated mucin MUC1 over-expressed in most epithelial tumor tissues is considered a promising target for immunotherapy. The extracellular part of MUC1 contains a domain of numerous tandem repeats of the amino acid sequence HGVTSAPDTRPAPGSTAPPA, including five potential O-glycosylation sites. In this study, T9 and S15 have been chosen as the positions of glycosylation. The glycopeptides N-terminally

在大多数上皮肿瘤组织中过度表达的肿瘤相关粘蛋白 MUC1 被认为是免疫治疗的有希望的靶点。MUC1 的细胞外部分包含氨基酸序列 HGVTSAPDTRAPPG STAPPA 的众多串联重复结构域，包括五个潜在的 O-糖基化位点。在本研究中，选择了 T9 和 S15 作为糖基化的位置。通过微波辅助 Fmoc 固相肽合成法合成了 N 端带有三甘醇间隔物的糖肽。从树脂上分离并脱保护后，将 MUC1 糖肽与牛血清白蛋白 (BSA) 结合。为了评估免疫学特性，用这些 BSA 疫苗免疫 balb/c 小鼠。
Synthetic Glycopeptides of the Tandem Repeat Sequence of the Epithelial Mucin MUC4 with Tumour-associated Carbohydrate Antigens

作者：Horst Kunz、Constanze Brocke

DOI：10.1055/s-2003-42029

日期：——

Glycohexadecapeptides representing the tandem repeat sequence of the epithelial mucin MUC4 were prepared by applying a solid-phase methodology. The required glycosyl amino acid building blocks containing the tumour-associated saccharide antigens TN-, T,- sialyl-TN, (2,6)- and (2,3)-sialyl-T were synthesized according to a straightforward biomimetic strategy by stepwise extension of the saccharide side chain of a Fmoc-protected galactosamine threonine tert-butyl ester.

通过采用固相方法学，制备了代表上皮粘蛋白MUC4串联重复序列的甘露肽。利用逐步延伸Fmoc保护的半乳糖胺苏氨酸叔丁酯糖侧链的简易仿生策略，合成了包含肿瘤相关糖抗原TN-、T-、唾液酸TN-、(2,6)-和(2,3)-唾液酸T的所需糖基氨基酸构建单元。