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47695

Sigma-Aldrich

Fmoc-Cys(Trt)-OH

≥95.0% (sum of enantiomers, HPLC)

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Synonym(s):
N-(9-Fluorenylmethoxycarbonyl)-S-trityl-L-cysteine, Nα-Fmoc-S-trityl-L-cysteine
Empirical Formula (Hill Notation):
C37H31NO4S
CAS Number:
Molecular Weight:
585.71
Beilstein:
4221286
MDL number:
eCl@ss:
32160406
PubChem Substance ID:
NACRES:
NA.26

Quality Level

Assay

≥95.0% (sum of enantiomers, HPLC)

optical activity

[α]20/D +16.0±2°, c = 1% in THF

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

mp

170-173 °C (lit.)

application(s)

peptide synthesis

functional group

Fmoc

storage temp.

2-8°C

SMILES string

OC(=O)[C@H](CSC(c1ccccc1)(c2ccccc2)c3ccccc3)NC(=O)OCC4c5ccccc5-c6ccccc46

InChI

1S/C37H31NO4S/c39-35(40)34(38-36(41)42-24-33-31-22-12-10-20-29(31)30-21-11-13-23-32(30)33)25-43-37(26-14-4-1-5-15-26,27-16-6-2-7-17-27)28-18-8-3-9-19-28/h1-23,33-34H,24-25H2,(H,38,41)(H,39,40)/t34-/m0/s1

InChI key

KLBPUVPNPAJWHZ-UMSFTDKQSA-N

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This Item
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Fmoc-Cys(Trt)-OH ≥95.0% (sum of enantiomers, HPLC)

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Fmoc-Cys(Trt)-OH

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Fmoc-Cys(Trt)-OH

Fmoc-Cys(StBu)-OH ≥95.0% (HPLC)

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Fmoc-Cys(StBu)-OH

Fmoc-Cys(tBu)-OH ≥98.0% (HPLC)

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47516

Fmoc-Cys(tBu)-OH

optical activity

[α]20/D +16.0±2°, c = 1% in THF

optical activity

-

optical activity

[α]20/D −83±2°, c = 1% in ethyl acetate

optical activity

-

mp

170-173 °C (lit.)

mp

164-175 °C

mp

73-77 °C

mp

-

functional group

Fmoc

functional group

thiol

functional group

Fmoc

functional group

Fmoc

storage temp.

2-8°C

storage temp.

−20°C (−15°C to −25°C)

storage temp.

2-8°C

storage temp.

2-8°C

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

General description

Fmoc-Cys(Trt)-OH is an amino acid commonly used in the Fmoc solid-phase peptide synthesis.

Application

Fmoc-Cys(Trt)-OH is an N-terminal protected cysteine derivative used in peptide synthesis. Some of the examples are:
  • Synthesis of mono- and bi-functionalized platinum(IV) complexes to target angiogenic tumor vasculature.
  • Synthesis of proteins through native chemical ligation of peptide hydrazides as thioester surrogates via solid-phase synthesis.
  • Synthesis of glycoconjugates by conjugating reducing sugars to cysteine residues of peptides.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Conjugated platinum (IV)? peptide complexes for targeting angiogenic tumor vasculature.
Mukhopadhyay S, et al.
Bioconjugate Chemistry, 19(1), 39-49 (2007)
A double-click approach to the protecting group free synthesis of glycoconjugates.
Alexander S R, et al.
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Parallel synthesis of structurally diverse aminobenzimidazole tethered sultams and benzothiazepinones
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Tetrahedron Letters, 53, 6897-6900 (2012)
Chemical synthesis of proteins using peptide hydrazides as thioester surrogates.
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Nature Protocols, 8(12), 2483-2483 (2013)
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Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology, 18(1), 198-207 (2018-11-14)
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