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Sigma-Aldrich

Boc-Cys(Npys)-OH

≥99.0% (TLC)

Synonym(s):

Nα-Boc-S-(3-nitro-2-pyridylthio)-L-cysteine

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About This Item

Empirical Formula (Hill Notation):
C13H17N3O6S2
CAS Number:
76880-29-0
Molecular Weight:
375.42
Beilstein:
3569570
MDL number:
MFCD00153301
UNSPSC Code:
12352200
PubChem Substance ID:
57647493

Assay

≥99.0% (TLC)

optical activity

[α]20/D −94±5°, c = 1% in methanol

mp

~160 °C (dec.)

application(s)

peptide synthesis

SMILES string

CC(C)(C)OC(=O)N[C@@H](CSSc1ncccc1[N+]([O-])=O)C(O)=O

InChI

1S/C13H17N3O6S2/c1-13(2,3)22-12(19)15-8(11(17)18)7-23-24-10-9(16(20)21)5-4-6-14-10/h4-6,8H,7H2,1-3H3,(H,15,19)(H,17,18)/t8-/m0/s1

InChI key

OVTLOLNDKQUMRH-QMMMGPOBSA-N

Storage Class Code

13 - Non 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

Certificates of Analysis (COA)

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G Mourier et al.
Journal of immunological methods, 171(1), 65-71 (1994-05-02)
Some T cell epitopes become inactive when their thiols are blocked with various irreversible reagents (Régnier-Vigouroux, 1988; Maillère, 1992; Maillère et al., 1993). Blocking protein and peptide thiols with BCNP (Boc-Cys(Npys)-OH) constitutes a most appropriate strategy when searching for thiol-containing
M S Bernatowicz et al.
International journal of peptide and protein research, 28(2), 107-112 (1986-08-01)
The 3-nitro-2-pyridinesulfenyl (Npys) derivative of cysteine was prepared and used to facilitate the formation of an unsymmetrical disulfide bond. Since this derivative is stable in trifluoroacetic acid:CH2 Cl2 (1:1) and anhydrous hydrogen fluoride, Boc-Cys(Npys) could be used directly in solid
J W Drijfhout et al.
International journal of peptide and protein research, 32(3), 161-166 (1988-09-01)
The disulfide bond in S-3-nitro-2-pyridinesulfenyl (S-Npys) compounds is stable towards the acid treatment used in solid-phase peptide synthesis, yet the liability of S-Npys-peptides towards nucleophiles enables the conjugation to proteins to proceed under mild conditions. Thus Boc-Cys(Npys)-OH was coupled as
Y Kitamura et al.
Molecular pharmacology, 38(2), 184-191 (1990-08-01)
To gain insight into the coupling mechanism of inhibitory receptors, 5-hydroxytryptamine1A receptors and alpha 2-adrenoceptors, with GTP-binding proteins (G proteins) in the central nervous system, we examined the effects of two 3-nitro-2-pyridinesulfenyl compounds, S-(3-nitro-2-pyridinesulfenyl)-L-cysteine [Cys(Npys)] and N-t-butoxy-carbonyl-S-(3-nitro-2-pyridinesulfenyl)-L-cysteine [Boc-Cys(Npys)], on 1)
Ayami Matsushima et al.
Biopolymers, 106(4), 460-469 (2016-06-09)
We previously showed that an antagonist-based peptide ligand, H-Cys(Npys)-Arg-Tyr-Tyr-Arg- Ile-Lys-NH2 , captures the free thiol groups in the ligand-binding site of the nociceptin receptor ORL1. However, the exact receptor sites of this thiol-disulfide exchange reaction have not been uncovered, although
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