A FACILE SYNTHESIS OF ORTHOGONALLY PROTECTED STEREOISOMERIC LANTHIONINES BY REGIOSELECTIVE RING-OPENING OF SERINE BETA-LACTONE DERIVATIVES

被引：61

作者：

SHAO, H ^{[1
]}

WANG, SHH ^{[1
]}

LEE, CW ^{[1
]}

OSAPAY, G ^{[1
]}

GOODMAN, M ^{[1
]}

机构：

[1] UNIV CALIF SAN DIEGO, DEPT CHEM & BIOCHEM, LA JOLLA, CA 92093 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1995年 / 60卷 / 10期

关键词：

D O I：

10.1021/jo00115a003

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[No abstract available]

引用

页码：2956 / 2957

页数：2

共 37 条

[21]

LEE C, 1995, IN PRESS PEPTIDES 23

[22] SHORT LIPOPEPTIDE, REPRESENTATIVE OF A NEW FAMILY OF IMMUNOLOGICAL ADJUVANTS DEVOID OF SUGAR [J].

MIGLIORESAMOUR, D ;

BOUCHAUDON, J ;

FLOCH, F ;

ZERIAL, A ;

NINET, L ;

WERNER, GH ;

JOLLES, P .

LIFE SCIENCES, 1980, 26 (11) :883-888

[23] STUDIES ON 2-AZIRIDINECARBOXYLIC ACID .9. CONVENIENT SYNTHESIS OF OPTICALLY-ACTIVE S-ALKYLCYSTEINE, THREO-S-ALKYL-BETA-METHYLCYSTEINE, AND LANTHIONINE DERIVATIVES VIA THE RING-OPENING REACTION OF AZIRIDINE BY SEVERAL THIOLS [J].

NAKAJIMA, K ;

ODA, H ;

OKAWA, K .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1983, 56 (02) :520-522

[24] NEW APPLICATION OF PEPTIDE CYCLIZATION ON AN OXIME RESIN (THE PCOR METHOD) - PREPARATION OF LANTHIONINE PEPTIDES [J].

OSAPAY, G ;

GOODMAN, M .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (21) :1599-1600

[25]

OSAPAY G, UNPUB INT J PEPT PRO

[26]

Pansare S. V., 1991, ORG SYNTH, V70, P1

[27] LANTHIONINE CHEMISTRY .4. SYNTHESIS OF DIASTEREOISOMERIC CYCLOLANTHIONYL DERIVATIVES [J].

PHOTAKI, I ;

SAMOUILIDIS, I ;

CARANIKAS, S ;

ZERVAS, L .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1979, (11) :2599-2605

[28] TRANSFORMATION OF SERINE TO CYSTEINE - BETA-ELIMINATION REACTIONS IN SERINE DERIVATIVES [J].

PHOTAKI, I .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1963, 85 (08) :1123-+

[29] SYNTHESIS AND CONFORMATIONAL PROPERTIES OF THE LANTHIONINE-BRIDGED OPIOID PEPTIDE [D-ALAL2,ALAL5]ENKEPHALIN AS DETERMINED BY NMR AND COMPUTER-SIMULATIONS [J].

POLINSKY, A ;

COONEY, MG ;

TOYPALMER, A ;

OSAPAY, G ;

GOODMAN, M .

JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (22) :4185-4194

[30]

SHIBA T, 1986, BIOPOLYMERS, V25, pS11

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