15554
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:
Molecular Weight:
375.42
PubChem Substance ID:
UNSPSC Code:
12352200
Beilstein/REAXYS Number:
3569570
MDL number:
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
13 - Non Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
Regulatory Information
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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
Controlled peptide-protein conjugation by means of 3-nitro-2-pyridinesulfenyl protection-activation.
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