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Merck
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주요 문서

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43720

Sigma-Aldrich

N,N′-Disuccinimidyl carbonate

≥95.0% (NMR), for peptide synthesis

동의어(들):

N-Succinimidyl carbonate, DSC, Di(N-succinimidyl) carbonate

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About This Item

실험식(Hill 표기법):
C9H8N2O7
CAS Number:
74124-79-1
Molecular Weight:
256.17
Beilstein:
1499137
EC Number:
277-730-3
MDL number:
MFCD00009767
UNSPSC 코드:
12352005
PubChem Substance ID:
329756382
NACRES:
NA.22

제품명

N,N′-Disuccinimidyl carbonate, purum, ≥95.0% (NMR)

grade

purum

Quality Level

200

분석

≥95.0% (NMR)

양식

powder

반응 적합성

reaction type: Carbonylations

불순물

~3% N-hydroxysuccinimide (NMR)

mp

190 °C (dec.) (lit.)

응용 분야

peptide synthesis

작용기

imide

저장 온도

−20°C

SMILES string

O=C1CCC(=O)N1OC(=O)ON2C(=O)CCC2=O

InChI

1S/C9H8N2O7/c12-5-1-2-6(13)10(5)17-9(16)18-11-7(14)3-4-8(11)15/h1-4H2

InChI key

PFYXSUNOLOJMDX-UHFFFAOYSA-N

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관련 카테고리

애플리케이션

N,N′-Disuccinimidyl carbonate (DSC) can be used to synthesize:
  • Various carbamate derivatives from primary and sterically hindered secondary alcohols by alkoxycarbonylation.
  • Active carbonate resins from 4-hydroxymethylpolystyrene and 4-hydroxymethyl-3-nitrobenzamido resins via hydroxy functional groups.
  • Aza-glycinyl dipeptides, important intermediates for the preparation of various azapeptides.

It may be also used:
  • In the two-step preparation of 5-(6-(azidomethyl)nicotinamido)pentanoic acid, a copper-chelating picolyl azide derivative.
  • To activate the hydroxyl group of the hapten, γ-hydroxyphenylbutazone (HPBZ) so that HPBZ can effectively bind with human serum albumin(HSA)-immunogen to form a hapten-protein conjugate.

기타 정보

Convenient reagent for preparing N-succinimidyl esters of N-protected amino acids and other acids; activated carbonate, e.g. synthesis of ureas and carbamates; coupling of ligands to proteins (via lysines).

픽토그램

Health hazardExclamation mark
GHS08,GHS07

신호어

Warning

유해 및 위험 성명서

H302,H319,H373

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - STOT RE 2 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point (°F)

Not applicable

Flash Point (°C)

Not applicable

개인 보호 장비

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

가장 최신 버전 중 하나를 선택하세요:

시험 성적서(COA)

Lot/Batch Number
BCCB6748
BCBW0349
BCBT6035
BCBS5912V
BCBS4774V

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특정 버전이 필요한 경우 로트 번호나 배치 번호로 특정 인증서를 찾을 수 있습니다.

COA 검색

이 제품을 이미 가지고 계십니까?

문서 라이브러리에서 최근에 구매한 제품에 대한 문서를 찾아보세요.

문서 라이브러리 방문

T. Kokubo et al.
Journal of the American Chemical Society, 109, 606-606 (1987)
N. Nimura et al.
Analytical Chemistry, 58, 2372-2372 (1986)
Arun K Ghosh et al.
Tetrahedron letters, 33(20), 2781-2784 (1992-05-12)
An efficient and mild method for alkoxycarbonylation of amines is described, utilizing commercially available N,N'-disuccinimidyl carbonate.
M Morpurgo et al.
Journal of biochemical and biophysical methods, 38(1), 17-28 (1999-03-17)
Ligands containing amino or hydroxyl groups were converted to their corresponding activated N-hydroxysuccinimidyl carbamate and carbonate by reaction with disuccinimidyl carbonate (DSC). The latter reagents can be used for the group-specific modification of primary amines as an alternative to the
A.K. Ghosh et al.
Tetrahedron Letters, 33, 2781-2781 (1992)
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문서

Coupling Reagents

In principle, the seemingly simple formation of a peptide bond can be accomplished using all the procedures available in organic chemistry for the synthesis of carboxylic acid amides. However, due to the presence of various functional groups in natural and unnatural amino acids and particularly the requirement for full retention of chiral integrity, the coupling of amino acids and peptides under mild conditions can be challenging. A plethora of coupling reagents has been developed superseding each other in efficiency and suitability for specific applications (e.g., solid-phase peptide synthesis or fragment condensation).

Coupling Reagents

In principle, the seemingly simple formation of a peptide bond can be accomplished using all the procedures available in organic chemistry for the synthesis of carboxylic acid amides. However, due to the presence of various functional groups in natural and unnatural amino acids and particularly the requirement for full retention of chiral integrity, the coupling of amino acids and peptides under mild conditions can be challenging. A plethora of coupling reagents has been developed superseding each other in efficiency and suitability for specific applications (e.g., solid-phase peptide synthesis or fragment condensation).

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