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773069

Fmoc-N-Me-Cys(Trt)-OH

97% (HPLC)

Synonym(s):

N-α-Fmoc-N-α-methyl-S-trityl-L-cysteine

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About This Item

Empirical Formula (Hill Notation):
C38H33NO4S
CAS Number:
944797-51-7
Molecular Weight:
599.74
MDL number:
MFCD11973909
UNSPSC Code:
12352209
NACRES:
NA.26
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Quality Level

100

assay

97% (HPLC)

form

powder or crystals

optical activity

[α]22/D -25.0°, c = 0.5% in dichloromethane

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

mp

234-239 °C

application(s)

peptide synthesis

functional group

Fmoc

storage temp.

2-8°C

SMILES string

S(C[C@H](N(C)C(=O)OCC4c5c(cccc5)c6c4cccc6)C(=O)O)C(c3ccccc3)(c2ccccc2)c1ccccc1

InChI

1S/C38H33NO4S/c1-39(37(42)43-25-34-32-23-13-11-21-30(32)31-22-12-14-24-33(31)34)35(36(40)41)26-44-38(27-15-5-2-6-16-27,28-17-7-3-8-18-28)29-19-9-4-10-20-29/h2-24,34-35H,25-26H2,1H3,(H,40,41)/t35-/m0/s1

InChI key

RAKOPMQMPUNRGI-DHUJRADRSA-N

Application

Fmoc-N-Me-Cys(Trt)-OH is a Fmoc-protected derivative of N-methyl cysteine used as a building block to prepare peptide thioesters under acidic conditions. The residue attached to the amino group of N-methylcysteine can migrate to the cysteinyl thiol group, resulting in the formation of a peptide thioester. The introduction of this Fmoc-protected derivative is best achieved using HATU as a coupling reagent in the presence of DIPEA (N, N-Diisopropylethylamine).
It can also be used to prepare Fmoc-N-Me-Cys(Trt)-OAllyl intermediate for the solid-phase synthesis of dithiol Triostin A.

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Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
MKCX5413
MKCR1605
MKCK9783
MKCG2370
MKCF2550

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Ganesh A Sable et al.
The Journal of organic chemistry, 80(15), 7486-7494 (2015-07-15)
Triostin A is a symmetric bicyclic depsipeptide with very potent antitumoral activity because of its bisintercalation into DNA. In this study, we report a new synthetic strategy that exploits a structural symmetry of triostin A. First, we prepared a novel

Global Trade Item Number

SKUGTIN
773069-1G04061826654781