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914002

Fmoc-Asp(CSY)-OH

≥95%

Synonym(s):

(S,Z)-4-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-4-carboxy-1-cyano-1-(dimethylsulfonio)but-1-en-2-olate, Asp with cyanosulfurylide (CSY)-protected carboxylic acid, Fmoc-protected aspartic acid for minimized aspartimide formation

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About This Item

Empirical Formula (Hill Notation):
C23H22N2O5S
CAS Number:
2379679-90-8
Molecular Weight:
438.50
MDL number:
MFCD32857296
UNSPSC Code:
12352209
NACRES:
NA.22
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Quality Level

100

assay

≥95%

form

powder

mp

157-162 °C

functional group

Fmoc

storage temp.

−20°C

SMILES string

[S+](C)(C)\C(=C(/[O-])\C[C@H](NC(=O)OCC1c2c(cccc2)c3c1cccc3)C(=O)O)\C#N

InChI

1S/C23H22N2O5S/c1-31(2)21(12-24)20(26)11-19(22(27)28)25-23(29)30-13-18-16-9-5-3-7-14(16)15-8-4-6-10-17(15)18/h3-10,18-19H,11,13H2,1-2H3,(H2-,25,26,27,28,29)/b21-20-/t19-/m0/s1

InChI key

CHPQTODSRMIOQS-WCZGFUKNSA-N

Application

Fmoc-Asp(CSY)-OH is an Fmoc-protected aspartic acid residue developed in the Bode Lab that contains a cyanosulfurylide (CSY) as a carboxylic-acid protecting group that completely suppresses aspartimide formation in peptide synthesis, a long-standing challenge in peptide chemistry that occurs during Fmoc removal or peptide coupling and affects peptide yield and sequences. Amenable to SPPS, deprotection is achieved under aqueous conditions with electrophilic halogenating agents to convert the ylide to the free acid. Furthermore, the hydrophilic nature of the ylide protecting group improves overall peptide efficiency and solubility.

Other Notes

Prevention of aspartimide formation during peptide synthesis using cyanosulfurylides as carboxylic acid-protecting groups

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
MKCM3668

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Kevin Neumann et al.
Nature communications, 11(1), 982-982 (2020-02-23)
Although peptide chemistry has made great progress, the frequent occurrence of aspartimide formation during peptide synthesis remains a formidable challenge. Aspartimide formation leads to low yields in addition to costly purification or even inaccessible peptide sequences. Here, we report an

Global Trade Item Number

SKUGTIN
914002-1G04061842116157
914002-250MG04061842116164