Nα-Boc-D-tryptophan N-hydroxysuccinimide ester
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Nα-Boc-D-tryptophan N-hydroxysuccinimide ester

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Category
BOC-Amino Acids
Catalog number
BAT-002922
CAS number
22220-11-7
Molecular Formula
C20H23N3O6
Molecular Weight
401.42
Nα-Boc-D-tryptophan N-hydroxysuccinimide ester
IUPAC Name
(2,5-dioxopyrrolidin-1-yl) (2R)-3-(1H-indol-3-yl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
Synonyms
Boc-D-Trp-OSu; (2,5-dioxopyrrolidin-1-yl)(2R)-3-(1H-indol-3-yl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate; Boc-D-tryptophan N-hydroxysuccinimide ester
Appearance
White to off-white powder
Purity
≥ 99% (HPLC)
Melting Point
143-150 °C
Storage
Store at 2-8 °C
InChI
InChI=1S/C20H23N3O6/c1-20(2,3)28-19(27)22-15(18(26)29-23-16(24)8-9-17(23)25)10-12-11-21-14-7-5-4-6-13(12)14/h4-7,11,15,21H,8-10H2,1-3H3,(H,22,27)/t15-/m1/s1
InChI Key
CPJXMXQYRHNIFU-OAHLLOKOSA-N
Canonical SMILES
CC(C)(C)OC(=O)NC(CC1=CNC2=CC=CC=C21)C(=O)ON3C(=O)CCC3=O
1.Selective Covalent Chemistry via Gas-Phase Ion/ion Reactions: An Exploration of the Energy Surfaces Associated with N-Hydroxysuccinimide Ester Reagents and Primary Amines and Guanidine Groups.
Bu J1, Fisher CM1, Gilbert JD1, Prentice BM1, McLuckey SA2. J Am Soc Mass Spectrom. 2016 Mar 28. [Epub ahead of print]
Selective covalent bond forming reactions (referred to as covalent reactions) can occur in gas-phase ion/ion reactions and take place via the formation of a long-lived chemical complex. The gas-phase ion/ion reactivity between sulfo-N-hydroxysuccinimide (sulfo-NHS) ester reagent anions and peptide cations containing a primary amine or guanidine group has been examined via DFT calculations and complex dissociation rate measurements. The results reveal insights regarding the roles of the barriers of competing processes within the complex. When the covalent reaction is exothermic, two prototypical cases, determined by the nature of the energy surface, are apparent. The product partitioning between covalent reaction and simple proton transfer upon dissociation of the long-lived complex is sensitive to activation conditions when the transition state barrier for covalent reaction is relatively high (case 1) but is insensitive to activation conditions when the transition state barrier is relatively low (case 2).
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